4-Chlorobenzenesulfonyl chloride → tert-Butyl 4-[(4-chlorobenzenesulphonylamino)methyl]piperidine-1-carboxylate

HRID 75107

Reaction equation

HRID 75107 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 86688412tert-Butyl 4-[(4-chlorobenzenesulphonylamino)methyl]piperidine-1-carboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.844 g (4 mmol) of 4-chlorobenzenesulphonyl chloride in 5 ml of dichloromethane is added dropwise to a solution of 0.857 g (4 mmol) of tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, 0.99 ml (6 mmol) of diisopropylethylamine and 0.024 g (0.2 mmol) of 4-dimethylaminopyridine in 9 ml of dichloromethane. The mixture is stirred at ambient temperature overnight. The organic phase is washed with 10 ml of water and then 4 ml of a 1N aqueous hydrochloric acid solution, 2 times 14 ml of water, 2 times 14 ml of a 1N aqueous sodium hydroxide solution, 3 times 14 ml of water and 14 ml of a saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness in order to obtain 1.371 g (3.52 mmol) of product in the form of an orange paste used as is in the following stage.

Workup

  1. washThe organic phase is washed with 10 ml of water
  2. dry with materialIt is dried over sodium sulphate
  3. customevaporated to dryness in order

Sources & evidence

ORD record
ord-30575c2547764b6dbeda56b31010f9e9
Source dataset
uspto-grants-2014_09
Patent number
US08835418B2

Linked notes

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