Phosgene → HCID 9917229, compound

HRID 1737235Notes

Reaction equation

HRID 1737235 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:34](Cl)(Cl)=[O:35].[NH2:38][C:39]1[CH:40]=[N:41][C:42]2[C:47]([CH:48]=1)=[CH:46][CH:45]=[CH:44][CH:43]=2>C(Cl)Cl>[CH3:14][CH:11]1[CH2:12][CH2:13][C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:34]([NH:38][C:39]3[CH:40]=[N:41][C:42]4[C:47]([CH:48]=3)=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:35])[CH:7]=[CH:6][CH:5]=2)([N:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH2:20]2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 113753-Aminoquinoline2×HCID 15434718HCID 15434718, compound

Product 1

HCID 9917229HCID 9917229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3-aminophenyl)-1-(4-phenylpiperazin-1-yl)-4-methyl-cyclohexane (cis isomer, 90 mg, 0.258 mmol) and triethylamine (90 μL, 0.65 mmol) in dry CH2Cl2 (7 mL) was brought to 0° C. using an ice bath. Phosgene (1.93 M in toluene, 160 μL) was added dropwise and the resulting mixture was stirred at 0° C., under a dry N2 atmosphere, for 30 minutes. 3-aminoquinoline (45 mg, 0.310 mmol) was added as a solid and the reaction was allowed to come to room temperature. Upon completion of the reaction (disappearance of 3-aminoquinoline) the mixture was diluted with an equal volume of CH2Cl2, washed with H2O, dried (Na2SO4) and concentrated to give the crude urea. Silica gel chromatography yielded pure N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)cyclohexyl]phenyl]-N'-3-quinolinyl-urea (cis isomer) as an off-white solid. The HCl salt was prepared by adding excess saturated EtOAc/HCl solution to the free base in dry MeOH. Concentration of the homogeneous solution yielded a solid which was washed with EtOAc. mp=180-181° C.

Workup

  1. customwas brought to 0° C.
  2. customto come to room temperature
  3. washwashed with H2O
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give the crude urea

Sources & evidence

ORD record
ord-c5c77164ee5c42adbdb356d232d75867
Source dataset
uspto-grants-1999_10
Patent number
US05962455

Reaction notes

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