3-Chloropropanesulphonyl chloride → 4-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

HRID 2365187Notes

Reaction equation

HRID 2365187 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:14][CH2:15][CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl.C(N(CC)CC)C>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([S:18]([CH2:17][CH2:16][CH2:15][Cl:14])(=[O:20])=[O:19])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 227098904-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 1-BOC-piperazine (6.00 g) in dry dichloromethane (60 ml) and triethylamine (5.85 ml) at 0° C. was added 3-chloropropanesulfonyl chloride (4.5 ml). The reaction mixture was stirred for 2 hours, diluted with dichloromethane, washed with brine, dried (MgSO4), filtered and volatiles removed in vacuo. Purification on silica gave 4-(3-chloro-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (9.85 g). This was reacted with dimethylamine hydrochloride in acetonitrile and potassium carbonate to give 4-(3-dimethylamino-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester. BOC-group was removed using HCl in ether under standard procedures to give the title compound.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customvolatiles removed in vacuo
  5. customPurification on silica

Sources & evidence

ORD record
ord-bf931319aa0f4c75915066a6d8e6fc2f
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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