Chloroform → 5-chloro-1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine

HRID 1014289Notes

Reaction equation

HRID 1014289 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:16])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[Cl:17]N1C(=O)CCC1=O.C(Cl)(Cl)Cl>C(#N)C>[Cl:17][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][C:13]=1[NH2:16])[N:7]([C:5](=[O:6])[CH2:4][N:2]([CH3:1])[CH3:3])[CH2:8][CH2:9]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 31398ChlorosuccinimideHCID 594419761-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine

Product 1

HCID 594416625-chloro-1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amineYield 15%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine (3.0 g, 13.68 mmol) in acetonitrile (150 mL) was treated with N-chlorosuccinimide (2.010 g, 15.05 mmol) and stirred at room temperature for 15 minutes. The solution was poured into chloroform/saturated sodium bicarbonate (aq.) and the organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford 5-chloro-1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine (0.510 g, 15% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.66 (s, 1 H), 7.01 (s, 1 H), 5.21 (s, 2 H), 4.08 (t, J=8.33 Hz, 2 H), 3.16 (s, 2 H), 2.95 (t, J=8.33 Hz, 2 H), 2.25 (s, 6 H).

Workup

  1. dry with materialthe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-69d9b202b16047fcb6556d8cd06c0e8b
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…