Triethylamine → N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(1-propyl-piperidin-4-yl)-benzamide

HRID 478643Notes

Reaction equation

HRID 478643 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2].Cl.[CH2:15]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[CH2:16][CH3:17].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:28](=[O:29])[C:27]2[CH:26]=[CH:25][C:24]([CH:21]3[CH2:20][CH2:19][N:18]([CH2:15][CH2:16][CH3:17])[CH2:23][CH2:22]3)=[CH:32][CH:31]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 111946841-Amino-cyclohexanecarboxylic acid cyanomethyl amideHCID 691302054-(1-Propyl-piperidin-4-yl)-benzoic acid hydrochloride

Product 1

HCID 10136279N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(1-propyl-piperidin-4-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Amino-cyclohexanecarboxylic acid cyanomethyl-amide (23 mmol), 4-(1-propyl-piperidin-4-yl)-benzoic acid hydrochloride (23 mmol), HOBT (23 mmol), WSCD (23 mmol) and triethylamine (23 mmol) are dissolved in DMF (50 ml) and stirred overnight at rt. After evaporation of the solvent, the residue is dissolved in a mixture of water and sodium carbonate (to ensure basic conditions) and extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is suspended in diethylether/pentane and the solid filtered of and dried (vacuum). A pale powder with mp. 198-200° C., Rf=0.34 (CH2Cl2/MeOH=9:1) is obtained.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue is dissolved in a mixture of water and sodium carbonate (to ensure basic conditions)
  3. extractionextracted three times with ethyl acetate
  4. extractionThe combined extract
  5. dry with materialis dried over sodium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA pale powder with mp. 198-200° C., Rf=0.34 (CH2Cl2/MeOH=9:1) is obtained

Sources & evidence

ORD record
ord-dd809ae9b7a94881bd297e984f49c042
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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