Chloroacetyl chloride → 4-[N'-(2-Chloro-acetyl)-hydrazinocarbonyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 20267Notes

Reaction equation

HRID 20267 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH2:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.[Cl:25][CH2:26][C:27](Cl)=[O:28]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH:17][C:27](=[O:28])[CH2:26][Cl:25])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 79724-MethylmorpholineHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Product 1

HCID 235440814-[N'-(2-Chloro-acetyl)-hydrazinocarbonyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (see reference WO 2000039125, prep 27)(25 g, 103 mmol) was dissolved in dichloromethane (300 ml) and 4-methylmorpholine (12.5 ml, 113 mmol) was then added. The mixture was cooled using an ice bath and chloroacetyl chloride (8.2 ml, 103 mmol) was added dropwise. The reaction was then allowed to warm to room temperature and was stirred for 4 hours. The reaction mixture was partitioned with aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate, filtered and the filtrate was evaporated to give the title compound as an off white solid (29.6 g).

Workup

  1. temperatureThe mixture was cooled
  2. customThe reaction mixture was partitioned with aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-963f709fee42487db197b25055a1c398
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Reaction notes

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