Benzoyl chloride → HCID 178523786, compound

HRID 728035Notes

Reaction equation

HRID 728035 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15][CH2:14]2)[CH2:9][CH2:8]1.C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([C@H:13]2[CH2:14][CH2:15][C@H:16]([NH:19][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:17][CH2:18]2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178511577HCID 178511577, compound

Product 1

HCID 178523786HCID 178523786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.8 g trans-4-[4-(2-pyridinyl)-1-piperazinyl]cyclohexylamine (Example 31a) in 100 mL of dichloromethane is added 4 mL of triethylamine and 2.84 mL of benzoyl chloride. The reaction mixture is refluxed under nitrogen for 1 hour. Saturated sodium bicarbonate solution is added. Some of the product comes out of solution at this point and is isolated by filtration. The organic layer is dried and evaporated to give 5.2 g of trans-N-[4-[4-(2-pyridinyl)-1-piperazinyl]cyclohexyl]benzamide; mp 241-244° C.

Workup

  1. temperatureThe reaction mixture is refluxed under nitrogen for 1 hour
  2. customis isolated by filtration
  3. customThe organic layer is dried
  4. customevaporated

Sources & evidence

ORD record
ord-acf08784daaf4beb8e60c593338700b9
Source dataset
uspto-grants-1991_09
Patent number
US05047406

Reaction notes

Loading…