1-Piperidinecarbonyl chloride → HCID 66815991, compound

HRID 1754954Notes

Reaction equation

HRID 1754954 reaction equation
[N:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[Cl:17][C:18]1[CH:19]=[C:20]([S:24]([N:27]2[CH2:43][CH2:42][C:30]3([N:34]=[C:33]([CH:35]4[CH2:40][CH2:39][CH2:38][NH:37][CH2:36]4)[NH:32][C:31]3=[O:41])[CH2:29][CH2:28]2)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>ClCCl>[Cl:17][C:18]1[CH:19]=[C:20]([S:24]([N:27]2[CH2:43][CH2:42][C:30]3([N:34]=[C:33]([CH:35]4[CH2:40][CH2:39][CH2:38][N:37]([C:7]([N:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[O:8])[CH2:36]4)[NH:32][C:31]3=[O:41])[CH2:29][CH2:28]2)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 2420851-Piperidinecarbonyl chlorideHCID 66817168HCID 66817168, compound

Product 1

HCID 66815991HCID 66815991, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (1.143 mmol, 3 eq) and piperidine-1-carbonyl chloride (0.457 mmol, 1.2 eq) were sequentially added to a mixed solution of 8-(3-chloro-benzenesulfonyl)-2-piperidin-3-yl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one trifluoroacetate (200 mg, 0.38 mmol) in dichloromethane (3 ml). The resulting mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The resulting residue was purified by HPLC to give 8-(3-chloro-benzenesulfonyl)-2-[1-(piperidine-1-carbonyl)-piperidin-3-yl]-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (30 mg, yield 15%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified by HPLC

Sources & evidence

ORD record
ord-9d348206c816410e84973a6680ee7be8
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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