Triethylamine → HCID 57964467, compound

HRID 2403548Notes

Reaction equation

HRID 2403548 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23](=[O:25])[CH3:24])[CH2:18][CH2:17]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>ClCCl>[CH2:37]([O:36][C:34](=[O:35])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23](=[O:25])[CH3:24])[CH2:18][CH2:17]3)[CH2:10][CH2:9]2)[CH:3]=1)[CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 57964583HCID 57964583, compound

Product 1

HCID 57964467HCID 57964467, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 0.1 g (0.3 mmol) of 1-(4-{2-[4-(3-aminophenyl)piperazin-1-yl]ethyl}piperidin-1-yl)propan-2-one in 5 mL of dichloromethane and 0.03 g (0.3 mmol) of triethylamine, is slowly added 0.032 g (0.3 mmol) of ethyl chloroformate. The mixture is stirred overnight at room temperature then concentrated under reduced pressure. The product is dissolved in ethyl acetate, washed twice with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The oily residue is purified over 10 g of silica gel (eluant dichloromethane/methanol 95/5) to give 0.025 g (20%) of [3-(4-{2-[1-(2-oxopropyl)piperidin-4-yl]ethyl}piperazin-1-yl)phenyl]carbamic acid ethyl ester as a solid.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe product is dissolved in ethyl acetate
  3. washwashed twice with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue is purified over 10 g of silica gel (eluant dichloromethane/methanol 95/5)

Sources & evidence

ORD record
ord-dd7053b0ba2d461582b02b545fc23aa6
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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