Triethylamine → HCID 45118641, compound

HRID 1726372Notes

Reaction equation

HRID 1726372 reaction equation
[NH2:1][CH:2]([CH3:13])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10](=O)[CH3:11])[CH2:6][CH2:5]1.C(N(CC)CC)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>>[NH2:1][CH:2]([CH3:13])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10](=[S:30])[CH3:11])[CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 87949Lawesson's reagentHCID 16787068HCID 16787068, compound

Product 1

HCID 45118641HCID 45118641, compound

Procedure

To a solution of 1-[4-(2-amino-propyl)-piperazin-1-yl]-ethanone (149 mg, 0.4 mmol) and triethylamine (TEA, 118 μl, 0.8 mmol) was added Lawesson's reagent (162 mg, 0.4 mmol) at RT. The reaction mixture was heated at reflux for 3 h to provide 1-[4-(2-aminopropyl)-piperazin-1-yl]-ethanethione (intermediate IVa). The solvent was evaporated and the residue was partitioned between ethyl ether and HCl (1 N), the organic layer was discarded and the aqueous layer was basified by addition of a saturated solution of K2CO3. The aqueous solution was extracted with ethyl acetate four times. The organic layers were combined, dried over sodium sulfate and evaporated. The crude mixture was used for the next coupling reaction. M+=202.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h

Sources & evidence

ORD record
ord-d7a65ba9e5dc4672991d60756f442ae9
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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