1-Pyrrolidinepropanamine → HCID 178512192, compound

HRID 1815441Notes

Reaction equation

HRID 1815441 reaction equation
I.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[NH:13])SC)=[CH:5][CH:4]=1.[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[NH:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 316701-PyrrolidinepropanamineHCID 178503999HCID 178503999, compound

Product 1

HCID 178512192HCID 178512192, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of step b (986 mg, 3.00 mmol) and N-(3-aminopropyl)-pyrrolidine (0.948 ml, 7.50 mmol) in ethanol (10 ml) was heated at reflux for 16 h. The solvent was removed at reduced pressure and the residue suspended in aqueous ammonia (880, 25 ml). The solid was removed by filtration and the filter-cake washed sequentially with water (50 ml) and diethyl ether (50 ml) to give the title compound as a white solid (585 mg, 69%). 1H NMR (DMSO-6) 7.18-7.12 (2H, m), 6.76-6.66 (2H, m), 5.8-4.8 (3H, br s), 3.12 (2H, t, 6.9), 2.43-2.36 (6H, m), 1.69-1.56 (6H, m). Microanalysis found C 60.01 H 7.62 N 19.74. C14H21ClN4 requires C 59.88 H 7.54 N 19.95.

Workup

  1. temperatureat reflux for 16 h
  2. customThe solvent was removed at reduced pressure
  3. customThe solid was removed by filtration
  4. washthe filter-cake washed sequentially with water (50 ml) and diethyl ether (50 ml)

Sources & evidence

ORD record
ord-94812d59394f483c90cc6f4428a96e4b
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

Loading…