1,2-Dichloroethane → 1-(2-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)-piperazine-2-carboxamide

HRID 1292345Notes

Reaction equation

HRID 1292345 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:19][C:20]([OH:22])=O.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH:32]([C:36]([NH2:38])=[O:37])[CH2:31]1.C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:11][CH2:12][N:13]([C:16](=[O:18])[CH3:17])[CH2:14][CH2:15]2)[CH:6]=[CH:5][C:4]=1[CH2:19][C:20]([N:33]1[CH2:34][CH2:35][N:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH3:23])[CH2:31][CH:32]1[C:36]([NH2:38])=[O:37])=[O:22]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 154305682-Carbamoyl-4-(2-methylphenyl)piperazineHCID 537598172-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetic acid

Product 1

HCID 536582201-(2-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)-piperazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetic acid (35 mg, 0.11 mmol), 4-(2-methylphenyl)piperazine-2-carboxamide (25 mg, 0.11 mmol), EDC (28 mg, 0.15 mmol), and HBT (17 mg, 0.13 mmol) were combined in DMF (4 ml) under nitrogen. The mixture was rendered basic by addition of triethylamine (0.043 ml) and stirred at ambient temperature for 18 hours. The mixture was concentrated in vacuo and the residue was chromatographed on silica gel eluted with 2% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo and the residue was rechromatographed on silica gel eluted with 96:4:0.4 methylene chloride:methanol:concentrated ammonia. The combined product fractions were evaporated to dryness in vacuo and the residue was concentrated from methanol and ether to give 1-(2-methoxy-4-(1-acetyl-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)-piperazine-2-carboxamide.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel
  3. washeluted with 2% methanol in methylene chloride
  4. customThe combined product fractions were evaporated to dryness in vacuo
  5. customthe residue was rechromatographed on silica gel
  6. washeluted with 96:4:0.4 methylene chloride
  7. customThe combined product fractions were evaporated to dryness in vacuo
  8. concentrationthe residue was concentrated from methanol and ether

Sources & evidence

ORD record
ord-6a518d9fc3194552b7398262badb0c08
Source dataset
uspto-grants-1998_05
Patent number
US05756504

Reaction notes

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