Benzoyl chloride → HCID 57888954, compound

HRID 1820285Notes

Reaction equation

HRID 1820285 reaction equation
[NH2:1][C@H:2]([CH:22]([CH3:24])[CH3:23])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([C:11]([O:13][CH3:14])=[O:12])[CH2:7][CH2:6]1)=[O:4].[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[C:25]([NH:1][C@H:2]([CH:22]([CH3:24])[CH3:23])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)([C:11]([O:13][CH3:14])=[O:12])[CH2:7][CH2:6]1)=[O:4])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 57889151HCID 57889151, compound

Product 1

HCID 57888954HCID 57888954, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-methyl 1-(2-amino-3-methylbutanoyl)-4-(4-chlorophenyl)piperidine-4-carboxylate (396 mg, 1.123 mmol) and benzoyl chloride (0.139 ml, 1.2 mmol) in CH2Cl2 (5 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.401 mL, 2.3 mmol). The mixture was stirred for 1 h at rt. The reaction was quenched with NaHCO3 (aq), extracted with dichloromethane, dried over Na2SO4 and concentrated. The residue was purified via column chromatography (20% EtOAc/heptane) to give (R)-methyl 1-(2-benzamido-3-methylbutanoyl)-4-(4-chlorophenyl)piperidine-4-carboxylate (467 mg, 91% yield) as a yellow solid.

Workup

  1. customThe reaction was quenched with NaHCO3 (aq)
  2. extractionextracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified via column chromatography (20% EtOAc/heptane)

Sources & evidence

ORD record
ord-792238d7697640a5b35f3626ee085341
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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