Hydrochloric Acid → HCID 67565561, compound

HRID 583133Notes

Reaction equation

HRID 583133 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][C:16](=[O:18])[N:15]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:14]=2)[C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:12]=1.[CH2:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C:26]1=O.C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CO.C(O)(=O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][C:16](=[O:18])[N:15]([CH:19]3[CH2:24][CH2:23][N:22]([CH:26]4[CH2:25][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH2:27]4)[CH2:21][CH2:20]3)[N:14]=2)[C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:12]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 119832-IndanoneHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 21310621HCID 21310621, compound

Product 1

HCID 67565561HCID 67565561, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

1.0 g (2.68 mmol) of 5-(6-chloro-3,4-dihydro-2H-benzopyran-8-yl) -3-(piperidin-4-yl) -1,3,4-oxadiazol-2(3H)-one hydrochloride is added to a solution of 1.13 g (8.60 mmol) of indan-2-one in 15 ml of methanol containing 0.169 ml of acetic acid, 0.709 g (1.13 mmol) of sodium cyanoborohydride is added at a temperature of 5° C. and the mixture is stirred for 18 h. 15 ml of aqueous hydrochloric acid are added and, after stirring for 30 min, the mixture is neutralized with 2M aqueous sodium hydroxide. The mixture is extracted with dichloromethane, the organic phase is separated and dried and the solvent is evaporated under reduced pressure. The residue is purified by preparative thin layer chromatography, elution being carried out with a 98/2 mixture of dichloromethane and methanol. A white solid is obtained, the hydrochloride of which is prepared in the usual way. 0.8 g of salt is isolated. Melting point: 283-284° C.

Workup

  1. additionis added at a temperature of 5° C.
  2. stirringafter stirring for 30 min
  3. extractionThe mixture is extracted with dichloromethane
  4. customthe organic phase is separated
  5. customdried
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is purified by preparative thin layer chromatography, elution
  8. additionbeing carried out with a 98/2 mixture of dichloromethane and methanol
  9. customA white solid is obtained

Sources & evidence

ORD record
ord-d5b8756741184e2d9180995196fbb1f7
Source dataset
uspto-grants-1999_07
Patent number
US05929089

Reaction notes

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