Triethylamine → N-{4-(1-hydroxyethyl)-1-(2-phenylethyl)-4-piperidinyl}-N-phenyl-cyclopropylcarboxamide

HRID 37371Notes

Reaction equation

HRID 37371 reaction equation
[OH:1][CH:2]([C:4]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)[CH3:3].[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1.C(N(CC)CC)C>C1C=CC=CC=1>[OH:1][CH:2]([C:4]1([N:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:28]([CH:25]2[CH2:27][CH2:26]2)=[O:29])[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5]1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 19935654HCID 19935654, compound

Product 1

HCID 19935657N-{4-(1-hydroxyethyl)-1-(2-phenylethyl)-4-piperidinyl}-N-phenyl-cyclopropylcarboxamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-(1-hydroxyethyl)-4-(N-phenylamino)-1-(2-phenylethyl)-piperidine (0.200 g), cyclopropylcarboxylic acid chloride (1 g) and triethylamine (2.2 g) in dry benzene (30 ml) was stirred for 2.5 hours at 60°-65° C. After cooling the mixture was washed with dilute sodium carbonate solution, dried over MgSO4 and then concentrated. The residue was chromatographed on silica gel using chloroform-methanol 76:1 as eluant to give the title compound (0.160 g), which with oxalic acid gave an oxalate salt, m.p. 158°-159° C.

Workup

  1. temperatureAfter cooling the mixture
  2. washwas washed with dilute sodium carbonate solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-df7e308664844494802ee9667d859efe
Source dataset
uspto-grants-1995_05
Patent number
US05420280

Reaction notes

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