Dimethylformamide dimethyl acetal → 4-(Dimethylamino)-3-[4-(4-phenyl-1-piperidinyl)phenyl]-3-buten-2-one

HRID 364941Notes

Reaction equation

HRID 364941 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH:25](OC)[N:26]([CH3:28])[CH3:27]>>[CH3:25][N:26]([CH3:28])[CH:27]=[C:19]([C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][CH2:11]2)=[CH:14][CH:15]=1)[C:20](=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 133942301-[4-(4-Phenyl-1-piperidinyl)phenyl]-2-propanone

Product 1

HCID 539028804-(Dimethylamino)-3-[4-(4-phenyl-1-piperidinyl)phenyl]-3-buten-2-one

Procedure

A mixture of 4.0 g of 1-[4-(4-phenyl-1-piperidinyl)phenyl]-2-propanone and 16 ml of dimethylformamide dimethylacetal is stirred at room temperature overnight, followed by heating at 45°-60° C. for six hours. The solvent is evaporated and the residue triturated with two 100 ml portions of hexane. The solid is filtered and dried to give 3.5 g of orange powder, mp 93°-100° C. Upon standing overnight at 0° C., the filtrate gave an additional 0.7 g of the product, mp 103.5°-105° C. This material is used directly for the next step without further purification.

Workup

  1. temperatureby heating at 45°-60° C. for six hours
  2. customThe solvent is evaporated
  3. customthe residue triturated with two 100 ml portions of hexane
  4. filtrationThe solid is filtered
  5. customdried

Sources & evidence

ORD record
ord-1680d7fc6d7f48b7835f3d42cbd5e7e6
Source dataset
uspto-grants-1986_08
Patent number
US04607037

Reaction notes

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