N-Benzylnormechlorethamine → 1-Benzyl-4-[4-(3-methyl-butoxy)-benzenesulfonyl]-piperidine-4-carboxylic acid ethyl ester

HRID 991122Notes

Reaction equation

HRID 991122 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2].Cl[CH2:23][CH2:24][N:25]([CH2:33][CH2:34]Cl)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:1]([O:3][C:4]([C:5]1([S:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:13][CH:14]=2)(=[O:7])=[O:8])[CH2:23][CH2:24][N:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:33][CH2:34]1)=[O:21])[CH3:2]

Participants

3

Reactant 2

HCID 5928N-BenzylnormechlorethamineHCID 11088330[4-(3-Methyl-butoxy)phenylsulfonyl]-acetic acid ethyl ester

Product 1

HCID 109068391-Benzyl-4-[4-(3-methyl-butoxy)-benzenesulfonyl]-piperidine-4-carboxylic acid ethyl ester

Procedure

1-Benzyl-4-[4-(3-methyl-butoxy)-benzenesulfonyl]-piperidine-4-carboxylic acid ethyl ester was prepared according to the general method outlined in example 83 starting from [4-(3- methyl-butoxy)-phenylsulfonyl]-acetic acid ethyl ester (6.2 g, 20 mmol) and bis-(2-chloro-ethyl)-benzyl amine (6.44 g, 24 mmol). Yield 8 g (84%); yellow oil; MS: 474 (M+H)+

Sources & evidence

ORD record
ord-177369290c1c4ca9ab7b359045ecac9d
Source dataset
uspto-grants-2002_10
Patent number
US06462073B2

Reaction notes

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