Benzyl Alcohol → HCID 86742164, compound

HRID 1252511Notes

Reaction equation

HRID 1252511 reaction equation
[O:1]=[C:2]1[CH:7]([C:8]([O:10][CH3:11])=[O:9])[CH2:6][C:5](=[O:12])[NH:4][CH:3]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[O:1]=[C:2]1[CH:7]([C:8]([O:10][CH2:11][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:9])[CH2:6][C:5](=[O:12])[NH:4][CH:3]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 244Benzyl AlcoholHCID 86742163HCID 86742163, compound

Product 1

HCID 86742164HCID 86742164, compound

Procedure

3,6-Dioxo-2-(phenylmethyl)-4-piperidinecarboxylic acid, methyl ester, 4 g (0.015 mole) was added to benzyl alcohol, 8.1 g (0.075 mole), and the mixture warmed to 170° for three hours. The mixture was cooled and the residue chromatographed using 200 g of silica gel and eluting with 500 ml of dichloromethane-methanol (98:2) to give (±)-3,6-dioxo-2-(phenylmethyl)-4-piperidinecarboxylic acid, phenylmethyl ester, 4.5 g; mp. 119°-120.5°.

Workup

  1. temperaturethe mixture warmed to 170° for three hours
  2. temperatureThe mixture was cooled
  3. customthe residue chromatographed
  4. washeluting with 500 ml of dichloromethane-methanol (98:2)

Sources & evidence

ORD record
ord-05e38476cb63490c84be7110ef103d2a
Source dataset
uspto-grants-1988_05
Patent number
US04743585

Reaction notes

Loading…