HCID 14851585, compound → HCID 19872168, compound

HRID 329435Notes

Reaction equation

HRID 329435 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[O:19]=[C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[NH:21]1.[CH3:30][CH2:31][C:32]([Cl:34])=[O:33]>ClCCl>[ClH:34].[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N:9]([CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:32](=[O:33])[CH:31]([CH3:30])[N:21]1[C:22](=[O:29])[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]1=[O:19]

Participants

4

Reactant 2

HCID 14851585HCID 14851585, compoundHCID 131715265HCID 131715265, compound

Product 1

HCID 19872168HCID 19872168, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 10 g of N-(2,6-dimethylphenyl)-3-pyridine propanamine in dichloromethane was cooled in an ice bath and was treated with 10.4 g of 2,3-dihydro-1,3-dioxo-1H -isoindole-alpha-methylacetyl chloride. The reaction mixture was stirred at 0° C. for 10 minutes and allowed to warm to room temperature overnight. The solvent was evaporated and the residue was crystallized from methanol-ether to give 15.6 g of rac.-2,3-dihydro-N -(2,6-dimethylphenyl)-alpha-methyl-1,3-dioxo-N-[3-(3-pyridinyl) propyl]-1H-isoindole-2-acetamide-hydrochloride, mp 220°-223° C. Recrystallization from methanol-ether afforded 13.55 g of captioned product, mp 223°-225° C.

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe solvent was evaporated
  3. customthe residue was crystallized from methanol-ether

Sources & evidence

ORD record
ord-4e09c678d4f34cbe950ebf16e2baedb2
Source dataset
uspto-grants-1990_01
Patent number
US04891429

Reaction notes

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