1-Chloroethyl chloroformate → HCID 68534030, compound

HRID 1172274Notes

Reaction equation

HRID 1172274 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:27]C(OC(Cl)C)=O>C(Cl)Cl>[ClH:27].[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[O:16])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 4064333N-(1-benzylpiperidin-4-yl)naphthalene-1-carboxamide

Product 1

HCID 68534030HCID 68534030, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(1-benzylpiperidin-4-yl)napth-1-yl carboxamide (1.38 g, 4.0 mmol) in dry CH2Cl2 (15 ml) was cooled to 0° C. and added α-chloroethyl chloroformate (1.14 g, 8.0 mmol) and stirred for 30 minutes. The mixture was evaporated in vacuo, added MeOH (15 ml) and heated under reflux for 1 h. The reaction mixture was evaporated in vacuo and the residue recrystallized from acetonitrile to give the product as a white powder (1.01 g, 86.8%).

Workup

  1. customThe mixture was evaporated in vacuo
  2. additionadded MeOH (15 ml)
  3. temperatureheated
  4. temperatureunder reflux for 1 h
  5. customThe reaction mixture was evaporated in vacuo
  6. customthe residue recrystallized from acetonitrile

Sources & evidence

ORD record
ord-704a08ebb6534118850f2d0f9bf7a3ce
Source dataset
uspto-grants-2010_11
Patent number
US07834010B2

Reaction notes

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