Phosgene → HCID 16071130, compound

HRID 2064210Notes

Reaction equation

HRID 2064210 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[C:4]([NH2:22])[CH:3]=1.[C:23](Cl)(Cl)=[O:24].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[N:9]([CH:10]3[CH2:15][CH2:14][N:13]([CH:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[CH2:12][CH2:11]3)[C:23](=[O:24])[NH:22][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 59850204HCID 59850204, compound

Product 1

HCID 16071130HCID 16071130, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(4,5-Dichloro-2-aminophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D39) (140 mg, 0.4 mmol) was dissolved in 10 ml of dichloromethane at 0° C. and phosgene (20% in toluene, 0.25 ml) and triethylamine (0.2 ml, 1.5 mmol) were added and the mixture was stirred at 0° C. for 1 h, then washed with aqueous sodium bicarbonate, dried over MgSO4, filtered and evaporated The product was chromatographed on silica gel eluting with methanol-dichloromethane mixtures, and then further purified by MDAP to yield 5,6-dichloro-1-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one, 22 mg, which was converted into the hydrochloride salt using 4M HCl in dioxan.

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated The product
  5. customwas chromatographed on silica gel eluting with methanol-dichloromethane mixtures
  6. customfurther purified by MDAP

Sources & evidence

ORD record
ord-70a10d9488544b78bb43fa51ed11b844
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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