Cyclopropylamine → 1-(2-methoxy-4-(1-(2-(N-cyclopropylamino)ethylsulfonyl)-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

HRID 128596Notes

Reaction equation

HRID 128596 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([S:16]([CH:19]=[CH2:20])(=[O:18])=[O:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:26][CH:25]1[C:37]([NH2:39])=[O:38])=[O:23].[CH:40]1([NH2:43])[CH2:42][CH2:41]1>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([S:16]([CH2:19][CH2:20][NH:43][CH:40]3[CH2:42][CH2:41]3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:26][CH:25]1[C:37]([NH2:39])=[O:38])=[O:23]

Participants

4

Reactant 2

HCID 69828Cyclopropylamine2×HCID 189141631-(2-Methoxy-4-(1-ethenylsulfonyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

Product 1

HCID 539106271-(2-methoxy-4-(1-(2-(N-cyclopropylamino)ethylsulfonyl)-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Methoxy-4-(1-ethenylsulfonyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide (69 mg, 0.12 mmol) was dissolved in methanol (4 ml), treated with cyclopropylamine (0.0072 ml, 10 mg, 0.18 mmol), and stirred at ambient temperature under nitrogen for 18 hours. An additional 0.014 ml of cyclopropylamine was added and the mixture stirred another 72 hours at ambient temperature. The reaction was concentrated in vacuo and the residue was chromatographed on silica gel eluted with 4% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo. The residue was reconcentrated from ether to give 1-(2-methoxy-4-(1-(2-(N-cyclopropylamino)ethylsulfonyl)-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide: mp 69°-110° C.

Workup

  1. stirringthe mixture stirred another 72 hours at ambient temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was chromatographed on silica gel
  4. washeluted with 4% methanol in methylene chloride
  5. customThe combined product fractions were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-c06057aa202843599c2e1eb8d1870433
Source dataset
uspto-grants-1995_11
Patent number
US05464788

Reaction notes

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