1,2-Dichloroethane → HCID 67560538, compound

HRID 400071Notes

Reaction equation

HRID 400071 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>ClCCl.C(OCC)(=O)C>[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:6]([NH2:8])=[O:5])[CH2:26][CH2:25]1.[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid

Product 1

HCID 67560538HCID 67560538, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-tert-butoxycarbonyl-4-phenyl-piperidine-4-carboxylic acid (14.5 g, 47.5 mmol) and N-methylpiperazine (12 mL, 108 mmol) in dichloromethane (450 mL), Add HOBt (8.0 g), EDC (11.2 g). After 18 hours, evaporate in vacuo to give a residue, dissolve the residue in ethyl acetate, and extract repeatedly with water. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give 1-tert-butoxycarbonyl-4-phenyl-piperidine-4-carboxylic acid 4-methylpiperazine-amide: Rf =0.33 (6% methanol/dichloromethane).

Workup

  1. customevaporate in vacuo
  2. customto give a residue
  3. extractionextract repeatedly with water
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b552274f5bb14c64bb71a378e38d2ef8
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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