1-Chloroethyl chloroformate → N-[4-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]-4'-(trifluoro-methyl)-[1,1'-biphenyl]-2-carboxamide

HRID 1804434Notes

Reaction equation

HRID 1804434 reaction equation
ClC(OC(Cl)C)=O.C1(C[N:15]2[CH2:20][CH:19]=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]4[C:31]([C:36]5[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=5)=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:29])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)C=CC=CC=1>ClCCCl>[NH:15]1[CH2:16][CH:17]=[C:18]([C:21]2[CH:22]=[CH:23][C:24]([NH:27][C:28]([C:30]3[C:31]([C:36]4[CH:37]=[CH:38][C:39]([C:42]([F:43])([F:44])[F:45])=[CH:40][CH:41]=4)=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:29])=[CH:25][CH:26]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 22499387N-[4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

Product 1

HCID 22499395N-[4-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]-4'-(trifluoro-methyl)-[1,1'-biphenyl]-2-carboxamideYield 126.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Chloroethyl chloroformate (0.078 mol) was added dropwise to a stirring mixture of intermediate (20) (0.039 mol) in 1,2-dichloro-ethane (500 ml). The mixture was stirred for 30 minutes and then stirred and refluxed overnight. The solvent was evaporated. Methanol (500 ml) was added. The mixture was stirred and refluxed overnight. The solvent was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dried, yielding 20.8 g of N-[4-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]-4′-(trifluoro-methyl)-[1,1′-biphenyl]-2-carboxamide (intermediate 21).

Workup

  1. stirringstirred
  2. temperaturerefluxed overnight
  3. customThe solvent was evaporated
  4. additionMethanol (500 ml) was added
  5. stirringThe mixture was stirred
  6. temperaturerefluxed overnight
  7. customThe solvent was evaporated
  8. customThe residue was triturated in DIPE
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-fedddda21c9946c4acc0d072665b6f68
Source dataset
uspto-grants-2013_01
Patent number
US08354402B2

Reaction notes

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