Phenylacetyl chloride → N-[1-[1,6-Dihydro-6-oxo-1-(phenylmethyl)-3-pyridinyl]cyclohexyl]benzeneacetamide

HRID 1111118Notes

Reaction equation

HRID 1111118 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1([C:18]2[CH:19]=[CH:20][C:21](=[O:31])[N:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CN(C1C=CN=CC=1)C.ClCCl>[O:31]=[C:21]1[N:22]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:23]=[C:18]([C:12]2([NH:11][C:8](=[O:9])[CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:19]=[CH:20]1

Participants

5

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 97957635-(1-aminocyclohexyl)-1-(phenylmethyl)-2(1H)-pyridinone

Product 1

HCID 14989572N-[1-[1,6-Dihydro-6-oxo-1-(phenylmethyl)-3-pyridinyl]cyclohexyl]benzeneacetamideYield 99.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Phenylacetyl chloride (1.6 g) was added to a well stirred suspension of 5-(1-aminocyclohexyl)-1-(phenylmethyl)-2(1H)-pyridinone (2.9 g), poly-4-vinylpyridine (2.1 g) and a catalytic amount of 4-(N,N-dimethylamino)pyridine in 70 ml of dichloromethane, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered and the filtrate concentrated to give 4.1 g of oil. Column chromatography (silica gel, elution with ethyl acetate) afforded 2.1 g of foam. Recrystallization from ethyl acetate/hexanes gave 1.7 g of analytically pure product as needles, m.p. 152°-153° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-821b229471d243d1937fef3d14aab827
Source dataset
uspto-grants-1990_12
Patent number
US04978663

Reaction notes

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