Diisopropylamine → HCID 178505141, compound

HRID 1023238Notes

Reaction equation

HRID 1023238 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(NC(C)C)(C)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl>[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]([NH:27][S:36]([CH3:35])(=[O:38])=[O:37])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[O:6][CH2:5]1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 31297Methanesulfonyl chlorideHCID 178478587HCID 178478587, compound2×

Product 1

HCID 178505141HCID 178505141, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 5 mL round-bottomed flask, Trans-4-[2-(4-Benzo[1,3]dioxol-4-yl-piperazin-1-yl)-ethyl]-cyclohexylamine hydrochloride (Intermediate A) (25 mg, 0.068 mmol) was solved in dichloromethane (500 μl) to give a white suspension. N,N-diisopropylamine (26.3 mg, 35.6 μl, 0.204 mmol) was added. and after 10 min stirring, methanesulfonyl chloride (11.7 mg, 7.89 μl, 0.102 mmol) was added and the reaction mixture was stirred over night at room temp. The reaction was quenched with 15 mL of saturated NaHCO3 and extracted with dichloromethane (3×20 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 white solid (18 mg, 64.3%), MS (ISP) m/z=410.3 [(M+H)+].

Workup

  1. customto give a white suspension
  2. stirringthe reaction mixture was stirred over night at room temp
  3. customThe reaction was quenched with 15 mL of saturated NaHCO3
  4. extractionextracted with dichloromethane (3×20 mL)
  5. dry with materialThe organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 10 g, 0% to 15% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-7bdf46109a014c92876877fcb6a77689
Source dataset
uspto-grants-2014_05
Patent number
US08722683B2

Reaction notes

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