Diethylamine → 1-(2-methoxy-4-(1-(2-(N,N-diethylamino)-ethylsulfonyl)-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

HRID 128595Notes

Reaction equation

HRID 128595 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].[CH2:40]([NH:42][CH2:43][CH3:44])[CH3:41]>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][N:42]([CH2:43][CH3:44])[CH2:40][CH3:41])(=[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 8021Diethylamine2×HCID 189141631-(2-Methoxy-4-(1-ethenylsulfonyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

Product 1

HCID 98306681-(2-methoxy-4-(1-(2-(N,N-diethylamino)-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 (52 mg, 0.093 mmol) was dissolved in methanol (5 ml), treated with diethylamine (0.013 ml, 9.2 mg, 0.12 mmol), and stirred at ambient temperature under nitrogen for 18 hours. An additional 0.01 ml of diethylamine was added and the mixture stirred another 24 hours at ambient temperature. The reaction was concentrated in vacuo and the residue was chromatographed on silica gel eluted with 3% followed by 5%, then 7% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo to give 1-(2-methoxy-4-(1-(2-(N,N-diethylamino)-ethylsulfonyl)-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide: mp 70°-140° C.

Workup

  1. stirringthe mixture stirred another 24 hours at ambient temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was chromatographed on silica gel
  4. washeluted with 3%
  5. customThe combined product fractions were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-6faf757ebfc9465097d21a46ef51cbac
Source dataset
uspto-grants-1995_11
Patent number
US05464788

Reaction notes

Loading…