Methyl chloroformate → HCID 178502261, compound

HRID 1023221Notes

Reaction equation

HRID 1023221 reaction equation
Cl.Cl.Cl.[O:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[O:6][CH2:5]1.C(N(CC)CC)C.[C:35](Cl)(=[O:38])[O:36][CH3:37]>ClCCl>[CH3:37][O:36][C:35](=[O:38])[NH:27][C@H:24]1[CH2:25][CH2:26][C@H:21]([CH2:20][CH2:19][N:16]2[CH2:17][CH2:18][N:13]([C:12]3[C:7]4[O:6][CH2:5][O:4][C:8]=4[CH:9]=[CH:10][CH:11]=3)[CH2:14][CH2:15]2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178478587HCID 178478587, compound2×

Product 1

HCID 178502261HCID 178502261, compoundYield 30,809.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared from Trans-4-[2-(4-Benzo[1,3]dioxol-4-yl-piperazin-1-yl)-ethyl]-cyclohexylamine hydrochloride (Intermediate A) (25 mg, 0.068 mmol) and triethylamine (20.6 mg, 28.4 μl, 204 μmol) in dichloromethane (1 mL). Methyl carbonochloridate (7.06 mg, 5.78 μl, 0.075 μmol) was added to the mixture stirring at 0° C. The ice bath was removed and the reaction mixture was stirred for 1 hour at room temp. The reaction was diluted with dichloromethane and quenched with sat NaHCO3 (4 mL). The aqueous layer was extracted with DCM (1×5 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 0% to 15% MeOH in dichloromethane) to yield the title compound as a white solid (9 mg, 34%), MS (ISP) m/z=390.3 [(M+H)+].

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred for 1 hour at room temp
  3. additionThe reaction was diluted with dichloromethane
  4. customquenched with sat NaHCO3 (4 mL)
  5. extractionThe aqueous layer was extracted with DCM (1×5 mL)
  6. dry with materialThe organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (silica gel, 10 g, 0% to 15% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-ca48f750bf954b248fb021f97574800c
Source dataset
uspto-grants-2014_05
Patent number
US08722683B2

Reaction notes

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