Propionyl chloride → HCID 86744622, compound

HRID 981971Notes

Reaction equation

HRID 981971 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[C:6]1([CH2:12][N:13]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:15]([O:26][CH3:27])[CH2:14]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl.[OH-].[Na+]>[C:20]1([N:19]([C@H:16]2[CH2:17][CH2:18][N:13]([CH2:12][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:14][C@H:15]2[O:26][CH3:27])[C:1](=[O:4])[CH2:2][CH3:3])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 62324Propionyl chlorideHCID 67896137HCID 67896137, compound

Product 1

HCID 86744622HCID 86744622, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Propionyl chloride (0.77 g, 8.3 mmol) was added to cis-1-phenylmethyl-3-methoxy-4-phenylaminopiperidine (7b, 1.6 g, 5.3 mmol) from Example 4 in 30 ml of dichloromethane. The reaction solution was stirred at room temperature overnight and subsequently diluted with 20ml of 10% sodium hydroxide solution. The organic layer was separated and the aqueous layer was extracted with 2×50 ml of dichloromethane. The combined organic layers were dried and concentrated under vacuum to yield 1.84 g (99%) of crude cis-N-phenyl-N-(1-phenylmethyl-3-methoxy-4-piperidinyl)propanamide (I).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 2×50 ml of dichloromethane
  3. customThe combined organic layers were dried
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e37618ccc0ed42bd92578b4e34a71f57
Source dataset
uspto-grants-1991_02
Patent number
US04994471

Reaction notes

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