1-Pyrrolidinepropanamine → HCID 178484961, compound

HRID 1815443Notes

Reaction equation

HRID 1815443 reaction equation
[I-].[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][NH:8][C:9](=[N:12][CH3:13])SC)=[CH:5][CH:4]=1.[N:16]1([CH2:21][CH2:22][CH2:23][NH2:24])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]([NH:12][CH3:13])=[N:24][CH2:23][CH2:22][CH2:21][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 316701-PyrrolidinepropanamineHCID 22500424HCID 22500424, compound

Product 1

HCID 178484961HCID 178484961, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from step b (358 mg, 1.00 mmol) and 3-pyrrolidin-1-yl-propylamine (0.19 ml) in ethanol (4 ml) was stirred at ambient temperature for 16 h followed by heating at reflux for 1 h. The solvent was removed at reduced pressure and the residue was partitioned between DCM (20 ml) and aqueous ammonia (880, 20 ml). The aqueous phase was extracted with further DCM (10 ml) and then discarded. The combined organic phases were washed twice with water (20 ml) and once with brine (20 ml). The organic phase was dried over anhydrous sodium sulfate and the filtrate evaporated to afford the title compound (225 mg, 73%). 1H NMR 7.40-7.29 (4H, m), 4.60 (2H, s), 3.42-3.47 (2H, m), 2.97 (3H, s), 2.50-2.44 (6H, m), 1.83-1.63 (6H, m).

Workup

  1. temperatureby heating
  2. temperatureat reflux for 1 h
  3. customThe solvent was removed at reduced pressure
  4. customthe residue was partitioned between DCM (20 ml) and aqueous ammonia (880, 20 ml)
  5. extractionThe aqueous phase was extracted with further DCM (10 ml)
  6. washThe combined organic phases were washed twice with water (20 ml) and once with brine (20 ml)
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a4e3dc445b0843a693c43d9eb93c3205
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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