2-Chloro-1-piperidine-1-yl-ethanone → HCID 24948829, compound

HRID 556452Notes

Reaction equation

HRID 556452 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].Br[C:12]1([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[NH:14][C:13]1=[O:22]>O>[Cl:21][C:17]1[CH:16]=[C:15]2[C:20]([C:12]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:13](=[O:22])[N:14]2[CH2:2][C:3](=[O:4])[N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 57507298HCID 57507298, compound

Product 1

HCID 24948829HCID 24948829, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the mixture of 2-chloro-1-piperidin-1-yl-ethanone (41 mg, 31 mmol) and KI (43 mg, 0.26 mmol) in dimethylformide (5 mL) was added rac-3-bromo-6-chloro-3-(4-chloro-benzyl)-1,3-dihydro-indol-2-one (100 mg, 0.26 mmol) prepared in example 76c. After stirring at room temperature for 2 h, water (10 mL) was added and the crude was extracted with ethyl acetate (3×20 mL). The combined organic solution was concentrated in vacuo. The residue was purified with preparative HPLC to give rac-6-chloro-3-(4-chloro-benzyl)-3-cyclohexylamino-1-(2-oxo-2-piperidin-1-yl-ethyl)-1,3-dihydro-indol-2-one as a white solid. MS: 514 (M+H)+.

Workup

  1. extractionthe crude was extracted with ethyl acetate (3×20 mL)
  2. concentrationThe combined organic solution was concentrated in vacuo
  3. customThe residue was purified with preparative HPLC

Sources & evidence

ORD record
ord-1635e389cd2043e68abae55d9b12eeb3
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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