Triethylamine → 1-(Benzocyclobuten-1-ylmethyl)-4-(2,4-difluorobenzoyl)piperidine

HRID 2372745Notes

Reaction equation

HRID 2372745 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].C1(C)C=CC(S(O[CH2:27][C:28]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH:29]=2)(=O)=O)=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:28]1([CH2:27][N:9]2[CH2:8][CH2:7][CH:6]([C:4](=[O:5])[C:3]3[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:2]=3[F:1])[CH2:11][CH2:10]2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13076388(2,4-Difluorophenyl)(piperidin-4-yl)methanoneHCID 19886368Benzocyclobuten-1-ylmethyl para-toluenesulfonate

Product 1

HCID 198863571-(Benzocyclobuten-1-ylmethyl)-4-(2,4-difluorobenzoyl)piperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.0019 mole of 4-(2,4-difluorobenzoyl)piperidine, 0.0019 mole of benzocyclobuten-1-ylmethyl para-toluenesulfonate and 0.04 mole of triethylamine dissolved in 50 ml of toluene are mixed and then brought to reflux for 18 hours. The reaction medium is then extracted with 1N hydrochloric acid and the aqueous phase is alkalinized and extracted with dichloromethane. The oil obtained is purified on a silica column using a mixture of cyclohexane and acetone (93:7 V/V) as eluent.

Workup

  1. additionare mixed
  2. temperatureto reflux for 18 hours
  3. extractionThe reaction medium is then extracted with 1N hydrochloric acid
  4. extractionextracted with dichloromethane
  5. customThe oil obtained
  6. customis purified on a silica column
  7. additiona mixture of cyclohexane and acetone (93:7 V/V) as eluent

Sources & evidence

ORD record
ord-f5eb0bff7d204453aad3f54dba98b3d2
Source dataset
uspto-grants-1992_03
Patent number
US05100902

Reaction notes

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