Dimethylamine → HCID 21270027, compound

HRID 1194344Notes

Reaction equation

HRID 1194344 reaction equation
[CH3:1][NH:2][CH3:3].Cl[CH2:5][CH2:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[CH3:18])=[O:8]>>[CH3:1][N:2]([CH3:3])[CH2:5][CH2:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[CH3:18])=[O:8]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 21270070HCID 21270070, compound

Product 1

HCID 21270027HCID 21270027, compound

Procedure

A solution of dimethylamine in IMS (33% w/v; 8 ml) was added to 3-chloro-1-(2-methyl-1H-indol-3-yl)-1-propanone (404 mg) and the mixture was left for 30 min. when a solid was precipitated. The mixture was refrigerated for 15 min. and the solid was filtered off and dried to give the title compound (207 mg). The mother liquors were evaporated to leave a solid which was partly dissolved in ethyl acetate (20 ml). Water (20 ml) was added and the solid remaining out of solution dissolved. The organic phase was extracted with 2M hydrochloric acid (3×20 ml) and the combined acidic extracts were brought to pH 10 with 0.88 ammonia solution. The mixture was extracted with ethyl acetate (3×25 ml), and the combined, dried organic extracts were evaporated to leave a solid which was crystallised from ethanol. The crystals were combined to give the title compound (386 mg), m.p. 172°-175°.

Workup

  1. customwas precipitated
  2. waitThe mixture was refrigerated for 15 min.
  3. filtrationthe solid was filtered off
  4. customdried

Sources & evidence

ORD record
ord-40e2e8c82a6740f3ae1427c71f397c23
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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