Triethylamine → Ammonia

HRID 375538Notes

Reaction equation

HRID 375538 reaction equation
[CH2:1]([O:5]C(Cl)=O)[CH:2](C)[CH3:3].[C:9]1([N:15]2[CH2:20][CH2:19][N:18](C(C)C(O)=O)[CH2:17][CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[CH2:33]([N:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[N:42]=[C:41]1[C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[NH3:15].[CH2:33]([N:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[N:42]=[C:41]1[C:49]1[CH:50]=[CH:51][C:52]([NH:55][C:1](=[O:5])[CH2:2][CH2:3][N:18]2[CH2:17][CH2:16][N:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:20][CH2:19]2)=[CH:53][CH:54]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 176058152-(4-Phenylpiperazin-1-yl)propanoic acidHCID 18993048HCID 18993048, compound

Product 2

HCID 222AmmoniaHCID 53702534HCID 53702534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

i-Butylchloroformate (0.24 mL) is added to 4-phenylpiperazin-1-ylpropanoic acid (0.39 g) and triethylamine (0.28 mL) in dichloromethane (10 mL) at -20° C. under nitrogen. After stirring for 30 minutes, 4-(1-benzyl-1H-benzimidazol-2-yl)phenylamine (Step A) (0.50 g) in dichloromethane (10 mL) is added dropwise at -20° C. and the mixture allowed to warm to room temperature with stirring. The mixture is diluted with dichloromethane (50 mL), washed with 2N sodium carbonate (50 mL), dried over MgSO4, filtered and evaporated to leave a yellow oil. This oil is purified by MPLC on silica gel eluting with 250:8:1 dichloromethane: ethanol: 0.880 aqueous ammonia to give 0.66 g of the title compound as a yellow foam.

Workup

  1. stirringwith stirring
  2. washwashed with 2N sodium carbonate (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto leave a yellow oil
  7. customThis oil is purified by MPLC on silica gel eluting with 250:8:1 dichloromethane

Sources & evidence

ORD record
ord-4a9eee507e8846d88d762849bb691d37
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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