8-Methoxy-2,3,4,5,6,7-hexahydroazocine → 3-[1-(1-Benzyl-4-piperidinyl)cyclopentyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine

HRID 502981Notes

Reaction equation

HRID 502981 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2([C:19]([NH:21][NH2:22])=O)[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2([C:19]3[N:32]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][C:25]4=[N:22][N:21]=3)[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 122610598-Methoxy-2,3,4,5,6,7-hexahydroazocineHCID 684669711-(1-Benzylpiperidin-4-yl)cyclopentane-1-carbohydrazide

Product 1

HCID 684668093-[1-(1-Benzyl-4-piperidinyl)cyclopentyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocineYield 34.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(1-Benzylpiperidin-4-yl)cyclopentane-1-carbohydrazide (573 mg) and 8-methoxy-2,3,4,5,6,7-hexahydroazocine (671 mg) were stirred in toluene (10 ml) at 110° C. for 21 hours. The reaction solution was subjected to evaporation under reduced pressure and the resulting crude product was purified by column chromatography (chloroform:methanol=97:3). The resulting solid washed with hexane to obtain 255 mg of 3-[1-(1-benzyl-4-piperidinyl)cyclopentyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (white solid).

Workup

  1. customThe reaction solution was subjected to evaporation under reduced pressure
  2. customthe resulting crude product was purified by column chromatography (chloroform:methanol=97:3)
  3. washThe resulting solid washed with hexane

Sources & evidence

ORD record
ord-747c29e8c85c433f87a6d4cfb164633b
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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