Benzoyl chloride → 4-Benzamido-1-(2-benzoyloxyethyl)piperidine

HRID 2419202Notes

Reaction equation

HRID 2419202 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([NH:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:10]([NH:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][O:27][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:21][CH2:20]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 203151761-(2-Hydroxyethyl)-4-benzamidopiperidine

Product 1

HCID 203151754-Benzamido-1-(2-benzoyloxyethyl)piperidineYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.4 Milliliters (0.012 mol) of benzoylchloride were added to a stirred solution of 2.48 grams (0.01 mol) of 4-benzamido-1-(2-hydroxyethyl)piperidine and 2.8 milliliters (0.02 mol) of triethylamine in 10 milliliters of dichloromethane. The solution was stirred at room temperature for 2 hours, then washed with water, dried and evaporated. The residue was crystallised from n-butyl acetate to give 2.5 grams (75% yield) of the title compound m.p. 139°-40° C. Treatment of a solution of the base in ethanol with ethanolic hydrogen chloride precipitated the hydrochloride, m.p. 217°-18° C.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customThe residue was crystallised from n-butyl acetate

Sources & evidence

ORD record
ord-56f7d3a66bf24851ad457838c707d613
Source dataset
uspto-grants-1978_08
Patent number
US04105666

Reaction notes

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