N-Methylcyclohexylamine → HCID 20401994, compound

HRID 1980571Notes

Reaction equation

HRID 1980571 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH:22]([O:29][CH2:30][CH3:31])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:17][CH2:16]3)(=[O:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:32][NH:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH3:32][N:33]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([N:15]3[CH2:16][CH2:17][N:18]([CH2:21][CH:22]([O:29][CH2:30][CH3:31])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:19][CH2:20]3)(=[O:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1)[CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 11430Potassium CarbonateHCID 13044649HCID 13044649, compound

Product 1

HCID 20401994HCID 20401994, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 50 ml of chloroform was dissolved 4.6 g of 1-(4-chloro-6-quinazolinesulfonyl)-4-(2-ethoxy-2-phenylethyl)piperazine, and to the solution were added 1.7 g of N-methyl-N-cyclohexylamine and 1 g of anhydrous potassium carbonate, and the mixture was stirred at a temperature of 20° C. to 25° C. for 3 hours. The reaction solution thus obtained was washed with water, dried with anhydrous potassium carbonate and then chloroform was distilled therefrom. The residue was subjected to the same silica gel-column chromatography as in Example 1 using chloroform as the solvent for purification to give 4.2 g of 1-[4-(N-methyl-N-cyclohexylamino)-6-quinazolinesulfonyl]-4-(2-ethoxy-2-phenylethyl)piperazine [i.e., Compound (19)] in a yield of 79%.

Workup

  1. customThe reaction solution thus obtained
  2. washwas washed with water
  3. dry with materialdried with anhydrous potassium carbonate
  4. distillationchloroform was distilled
  5. customThe residue was subjected to the same silica gel-column chromatography as in Example 1 using chloroform as the solvent for purification

Sources & evidence

ORD record
ord-6d83824fc20e423bb89bc0542e214af1
Source dataset
uspto-grants-1985_04
Patent number
US04510307

Reaction notes

Loading…