Benzoyl chloride → HCID 22129672, compound

HRID 1857657Notes

Reaction equation

HRID 1857657 reaction equation
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]([N:28]2[CH2:33][CH2:32][C:31]([OH:40])([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:30][CH2:29]2)[CH2:26][NH2:27])[CH:21]=[CH:22][C:23]=1[Cl:24]>O1CCCC1>[ClH:9].[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]([N:28]2[CH2:29][CH2:30][C:31]([OH:40])([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:32][CH2:33]2)[CH2:26][NH:27][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:21]=[CH:22][C:23]=1[Cl:24]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22129659HCID 22129659, compound

Product 1

HCID 22129672HCID 22129672, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

Benzoyl chloride (290 mg) and triethylamine (420 mg) were added to a solution of 2-(3,4-Dichlorophenyl)-2-(4-hydroxy-4-phenyl-piperidino)ethylamine (750 mg) in tetrahydrofuran (37.5 mL). The reaction was stirred at 23° C. for 18 hours, and was evaporated to an oil-solid mixture. The mixture was partitioned between water (100 mL) and dichloromethane (100 mL), and the separated organic layer was dried and evaporated to an off-white solid (1.01 gm). Treatment of a solution of this solid in diethylether with hydrochloric acid (g)/diethylether followed by recrystalization of the hydrochloride salt from ethylacetate (hot,minimum volume) provided the title compound as a white solid (450 mg); mp 232-235° C.; MS: m/z=469(M+1); NMR: 1.8 (m,2), 2.44 (m,1), 2.63 (m,1), 3.17 (m,3), 3.99 (m,2), 4.27 (m,1), 4.76 (m,1), 5.4 (broad s,1), 7.26 (m,1), 7.46 (m,7), 7.8 (m,5), 11.37 (broad s,1). Analysis Calculated: C, 61.73; H, 5.38; N, 5.54; Found: C, 61.8; H, 5.5; N, 5.52.

Workup

  1. customwas evaporated to an oil-solid mixture
  2. customThe mixture was partitioned between water (100 mL) and dichloromethane (100 mL)
  3. customthe separated organic layer was dried
  4. customevaporated to an off-white solid (1.01 gm)
  5. customTreatment of a solution of this solid in diethylether with hydrochloric acid (g)/diethylether followed by recrystalization of the hydrochloride salt from ethylacetate (hot,minimum volume)

Sources & evidence

ORD record
ord-600a26cf24b049cb828610dbaa626b0d
Source dataset
uspto-grants-2000_11
Patent number
US06147083

Reaction notes

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