Phosgene → HCID 15886820, compound

HRID 1602853Notes

Reaction equation

HRID 1602853 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].[O:38]1[C:42]2([CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[O:41][CH2:40][CH2:39]1>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]([N:45]3[CH2:46][CH2:47][C:42]4([O:41][CH2:40][CH2:39][O:38]4)[CH2:43][CH2:44]3)=[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 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 15434718HCID 15434718, compound

Product 1

HCID 15886820HCID 15886820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(3-aminophenyl)-1-(4-phenylpiperazin-1-yl)-4-methyl-cyclohexane (cis isomer, 246 mg, 0.705 mmol) and triethylamine (147 μL, 1.06 mmol) in dry CH2Cl2 (15 mL) was brought to 020 C. using an ice bath. Phosgene (1.93 M in toluene, 438 μL, 0.846 mmol) was added dropwise and the resulting mixture was stirred at 020 C., under a dry N2 atmosphere, for 30 minutes. 1,4-dioxa-8-azaspiro[4.5]decane (181 μl 1.41 mmol) was added via syringe and the reaction was allowed to come to room temperature. After 2 h the reaction mixture was diluted with an equal volume of CH2Cl2, washed with H2O, dried (Na2SO4) and concentrated to give an off-white solid. The solid was washed with 30% EtOAc/hexanes to give the free base of N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)cyclohexyl]phenyl]-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxamide (cis isomer) as a white solid. mp=245-247° C.

Workup

  1. customto come to room temperature
  2. washwashed with H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give an off-white solid
  6. washThe solid was washed with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-77d3c74e9dfb40e99ccef450840833df
Source dataset
uspto-grants-1999_11
Patent number
US05985873

Reaction notes

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