4-Methylmorpholine → N'2-acetyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbohydrazide

HRID 397664Notes

Reaction equation

HRID 397664 reaction equation
O.ON1C2C=CC=CC=2N=N1.[C:12]([NH:15][NH2:16])(=[O:14])[CH3:13].CN1CCOCC1.CN(C)CCCN=C=NCC.[F:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([N:45]2[CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]2[C:51](O)=[O:52])(=[O:44])=[O:43])=[CH:38][CH:37]=1>ClCCl>[C:12]([NH:15][NH:16][C:51]([C@@H:46]1[CH2:47][CH2:48][CH2:49][CH2:50][N:45]1[S:42]([C:39]1[CH:38]=[CH:37][C:36]([F:35])=[CH:41][CH:40]=1)(=[O:44])=[O:43])=[O:52])(=[O:14])[CH3:13]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 14039AcetohydrazideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 768662(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 57053283N'2-acetyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbohydrazideYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Hydroxybenzotriazole hydrate (162 mg), acethydrazide (81 mg), N-methylmorpholine (275 μl) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (230 mg) were added to a stirred solution of (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acid [see Preparation 38] (287 mg) in dichloromethane (3 ml). The reaction mixture was stirred for 3 hours after which time the mixture was partitioned between dichloromethane and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure to afford N′2-acetyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbohydrazide (340 mg) as a white solid.

Workup

  1. customwas partitioned between dichloromethane and water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-fccb8fef80894d168aa330d44a040911
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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