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Dichloromethane → 3,4-Dihydro-9-(4,4-diphenylbutylamino)acridin-1(2H)-one

HRID 1249415
Notes
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Reaction equation

HRID 1249415 reaction equation
ClCCl.[OH-].[Na+].[NH2:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.S(O[CH2:27][CH2:28][CH2:29][CH:30]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(C)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:31]1([CH:30]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:29][CH2:28][CH2:27][NH:6][C:7]2[C:8]3[C:13]([N:14]=[C:15]4[C:20]=2[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]4)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-oneHCID 138807014,4-Diphenylbutyl methanesulfonate

Product 1

HCID 137560583,4-Dihydro-9-(4,4-diphenylbutylamino)acridin-1(2H)-oneYield 8%

Reagents, catalysts & solvents 2

HCID 94433
Tetrabutylammonium hydrogen sulfate
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
3 °C

Procedure

In a mixture consisting of 480 ml of dichloromethane and 320 ml of 50% NaOH were combined 8.00g of 9-amino-3,4-dihydroacridin-1(2H)-one, 68 g (6 eq) of 1-mesyloxy-4,4-diphenylbutane and 2.56 g (0.20 eq) of tetrabutylammonium hydrogensulfate used as a phase transfer catalyst. The biphasic mixture was jacket cooled to 3° C. and was then mechanically stirred for 3 days. As no further reaction occurred, the reaction mixture was diluted with water and the organic phase was separated. Analysis by thin layer chromatography indicated a 1:1 mixture of the end product and the starting material. The dichloromethane layer was evaporated to a gum. The gum was diluted with dichloromethane and mixed with 1:1 alumina/sand to immobilize it as a solid for Soxhlet extraction. The dichloromethane was evaporated and the solid was put into a Soxhlet extraction thimble and extracted with hexane for 4 hours. Since no further extraction occurred after 4 hours, the hexane solution was evaporated to an oil. The oil was chromatographed over silica gel (EtOAc) and the resultant solid rechromatographed through alumina (Et2O) to yield a solid. The solid was recrystallized from Et2O/hexanes to yield 1.22 g (8%) of product, melting point 86°-88° C.

Workup

  1. customAs no further reaction
  2. customthe organic phase was separated
  3. additiona 1:1 mixture of the end product
  4. customThe dichloromethane layer was evaporated to a gum
  5. additionThe gum was diluted with dichloromethane
  6. additionmixed with 1:1 alumina/sand
  7. extractionfor Soxhlet extraction
  8. customThe dichloromethane was evaporated
  9. extractionthe solid was put into a Soxhlet extraction thimble
  10. extractionextracted with hexane for 4 hours
  11. extractionSince no further extraction
  12. waitoccurred after 4 hours
  13. customthe hexane solution was evaporated to an oil
  14. customThe oil was chromatographed over silica gel (EtOAc)
  15. customthe resultant solid rechromatographed through alumina (Et2O)
  16. customto yield a solid
  17. customThe solid was recrystallized from Et2O/hexanes

Sources & evidence

ORD record
ord-a8dbde653ea9420abc3e665a7adbb7af
Source dataset
uspto-grants-1986_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04631286

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes