Potassium Carbonate → HCID 18627847, compound

HRID 1684341Notes

Reaction equation

HRID 1684341 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][CH2:9][CH2:10][C:11]#[N:12].[NH2:13][CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1>C(#N)C>[C:11]([CH2:10][CH2:9][CH2:8][NH:13][CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)#[N:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123364-Chlorobutyronitrile2×HCID 123445(+-)-1-Aminoindan

Product 1

HCID 18627847HCID 18627847, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (15.5 g, 112 mmole) and 4-chlorobutyronitrile (11.58 g, 112 mmole) was added to a solution of 1-aminoindan (5.0 g, 37.6 mmole) in acetonitrile (50 ml), and the mixture refluxed for 2 hr. A second portion of 4-chlorobutyronitrile (5.0 g) was then added, the mixture further heated for 24 hr, filtered and the filtrate evaporated to dryness. Unreacted 4-chlorobutyronitrile was removed by treating the residue (20 g) with isopropanolic HCl (16.7 ml, 24%) followed by successive extractions with ether (3×150 ml). The crude product thus obtained was further purified by column chromatography (Silica, CH2Cl2 :MeOH 98:2) to afford 3.7 g (49%) of tan-colored crystalline mass.

Workup

  1. temperaturethe mixture refluxed for 2 hr
  2. temperaturethe mixture further heated for 24 hr
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness
  5. customwas removed
  6. additionby treating the residue (20 g) with isopropanolic HCl (16.7 ml, 24%)
  7. extractionfollowed by successive extractions with ether (3×150 ml)

Sources & evidence

ORD record
ord-a5a495d4a0ce4159b3e60b632f36326f
Source dataset
uspto-grants-1997_06
Patent number
US05639913

Reaction notes

Loading…