(R)-(+)-3-Chlorostyrene oxide → 4-(4-[2-[(2R)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic acid octylamide

HRID 396014Notes

Reaction equation

HRID 396014 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:27]=[CH:26][C:7]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[Cl:28][C:29]1[CH:30]=[C:31]([C@@H:35]2[CH2:37][O:36]2)[CH:32]=[CH:33][CH:34]=1>C(Cl)(Cl)Cl.CO>[CH2:18]([NH:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9]([NH:8][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][NH:1][CH2:37][C@@H:35]([C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([Cl:28])[CH:30]=3)[OH:36])=[CH:27][CH:26]=2)[CH2:10][CH2:11]1)=[O:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 181736624-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide

Product 1

HCID 101866874-(4-[2-[(2R)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic acid octylamideYield 16.1%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide (0.50 g, 1.18 mmol) was reacted with (2R)-2-(3-chlorophenyl)oxirane (0.183 g, 1.18 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.063 g, 0.19 mmol).

Sources & evidence

ORD record
ord-e2fd099d977e4c8f879121edb2c9a30c
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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