Cyclopropanemethanamine → HCID 57479058, compound

HRID 556465Notes

Reaction equation

HRID 556465 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.Br[C:7]1([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[C:15]2[C:10](=[CH:11][C:12]([Cl:16])=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:17]>ClCCl>[Cl:16][C:12]1[CH:11]=[C:10]2[C:15]([C:7]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([NH:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:8](=[O:17])[NH:9]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 57479058HCID 57479058, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cyclopropanemethylamine (142 mg, 2.0 mmol) in dichloromethane (20 mL) was added rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (0.37 g, 0.99 mmol). After the mixture was stirred at room temperature for 1 h, another portion of dichloromethane (20 mL) was added. The mixture was washed with water (20 mL×2). The organic layer was separated, dried over Na2SO4 and concentrated to give 0.34 g of rac-6-chloro-3-(3-chloro-benzyl)-3-(cyclopropylmethyl-amino)-1,3-dihydro-indol-2-one as a white solid. MS: [M+H]+=361

Workup

  1. washThe mixture was washed with water (20 mL×2)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb01ae7848174c4da1638c34c93f7de1
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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