Chlorosuccinimide → Jnj-40411813

HRID 2276325Notes

Reaction equation

HRID 2276325 reaction equation
[CH2:1]([N:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].[Cl:24]N1C(=O)CCC1=O>C(Cl)Cl>[CH2:1]([N:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:16]2)=[C:7]([Cl:24])[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 594970911-butyl-4-(4-phenylpiperidin-1-yl)pyridin-2(1H)-one

Product 1

HCID 25195461Jnj-40411813Yield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of intermediate D19 (0.43 g, 1.40 mmol) and N-chlorosuccinimide (0.19 g, 1.40 mmol) in DCM (10 ml) was stirred at room temperature for 1 hour. The solvent was evaporated in vacuo and the crude product was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent). The desired fractions were collected and evaporated in vacuo and the resulting solid was recrystallized from diethyl ether to yield compound E2 (0.39 g, 82%) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude product was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent)
  3. customThe desired fractions were collected
  4. customevaporated in vacuo
  5. customthe resulting solid was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-a64dc465a77d4d8892ef6b607ea97c32
Source dataset
uspto-grants-2015_09
Patent number
US09132122B2

Reaction notes

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