Hydrochloric Acid → 135729-56-5

HRID 1590128Notes

Reaction equation

HRID 1590128 reaction equation
[CH2:1]([Li])CCC.CCCCCC.[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@H:14]([NH:20][C:21]([C:23]1[C:32]3[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=3[CH:26]=[CH:25][CH:24]=1)=[O:22])[CH2:13]2.CN(C)C=O.Cl>O1CCCC1>[N:12]12[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19]1)[C@H:14]([N:20]1[CH:1]=[C:31]3[CH2:30][CH2:29][CH2:28][C:27]4[C:32]3=[C:23]([CH:24]=[CH:25][CH:26]=4)[C:21]1=[O:22])[CH2:13]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8058HexaneHCID 15656845135729-78-1HCID 178418339Butyllithium

Product 1

HCID 148210135729-56-5Yield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of n-butyllithium in hexane (60 mmol) was added dropwise at -70° C. to a solution of (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro1-naphthalenecarboxamide (7.70 g, 21 mmol), prepared as in Example 3, in dry tetrahydrofuran (400 mL). The reaction mixture was stirred at -10° C. for one hour, cooled to -70° C., and dimethylformamide (100 mmol) added in one portion. The reaction mixture was allowed to warm to room temperature over 1.5 hours, then cooled to 0° C. and acidified with 10% aqueous hydrochloric acid. The layers were separated, and the aqueous layer was washed with ethyl acetate, then made basic with 10N aqueous sodium hydroxide and extracted with ethyl acetate. The ethyl acetate was dried over anhydrous sodium sulfate, filtered, and evaporated to give 7.58 g (95% yield) of (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro1H-benz[de]isoquinolin-1-one as white crystals; m.p. 117°-118° C.; [α]D25 +43.2° (c=0.98, CHCl3).

Workup

  1. temperaturecooled to -70° C.
  2. temperatureto warm to room temperature over 1.5 hours
  3. temperaturecooled to 0° C.
  4. customThe layers were separated
  5. washthe aqueous layer was washed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. dry with materialThe ethyl acetate was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-b08891380cde4ea6bdb903972163b29a
Source dataset
uspto-grants-1993_04
Patent number
US05202333

Reaction notes

Loading…