Benzoyl chloride → [3-(3,4-Dichlorophenyl)-3-(3-hydroxy-propyl)-piperidin-1-yl]-phenyl-methanone

HRID 394547Notes

Reaction equation

HRID 394547 reaction equation
C(N(C(C)C)CC)(C)C.CC1(C)C2CC[C@@]1(CS([O:23][CH2:24][CH2:25][CH2:26][C@@:27]1([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]1)(=O)=O)C(=O)C2.[C:42]1([C:48](Cl)=[O:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(Cl)Cl>[Cl:40][C:35]1[CH:34]=[C:33]([C:27]2([CH2:26][CH2:25][CH2:24][OH:23])[CH2:32][CH2:31][CH2:30][N:29]([C:48]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:49])[CH2:28]2)[CH:38]=[CH:37][C:36]=1[Cl:39]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 131724007(R)-3-[3-(3,4-Dichlorophenyl)-piperidin-3-yl]-propan-1-ol(1s)-7,7-dimethyl-2-oxobicyclo[2,2,1]heptane-1-methanesulfonate

Product 1

HCID 22741724[3-(3,4-Dichlorophenyl)-3-(3-hydroxy-propyl)-piperidin-1-yl]-phenyl-methanoneYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine(5.7 mL, 3.27 mmol, 5.0 eq) was added to a mixture of camphorsulfonate salt (9) (3.4 g, 6.53 mmol) in CH2Cl2 (21 mL, 0.3 M) and followed by dropwise addition of PhCOCl (0.83 mL, 7.19 mmol, 1.1 eq). The solution was stirred at room temperature for 1 hour. The reacting mixture was diluted with CH2Cl2 (200 mL) and washed with brine, 1 M KHSO4, and saturated NaHCO3 then dried over MgSO4. The concentrated crude oil was purified by flash chromatography (CH2Cl2-MeOH/95:5) to give white solid (2.30 g, 89.8%).

Workup

  1. washwashed with brine, 1 M KHSO4, and saturated NaHCO3
  2. dry with materialthen dried over MgSO4
  3. concentrationThe concentrated crude oil
  4. customwas purified by flash chromatography (CH2Cl2-MeOH/95:5)

Sources & evidence

ORD record
ord-ebda47b7e3ba4ce1b5ae61b0d6bbbf8d
Source dataset
uspto-grants-2003_08
Patent number
US06602886B2

Reaction notes

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