Diisopropylethylamine → HCID 178483793, compound

HRID 2118233Notes

Reaction equation

HRID 2118233 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]([CH3:18])[C:6](=[O:17])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][CH3:16])[CH2:11][CH2:10]1.C(N(CC)C(C)C)(C)C.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][CH:34]=1)=[O:31].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:39][C:36]1[CH:37]=[CH:38][C:33]([O:32][C:30](=[O:31])[N:15]([C@H:12]2[CH2:11][CH2:10][C@H:9]([O:8][CH2:7][C:6](=[O:17])[N:5]([CH2:4][CH2:3][N:2]([CH3:19])[CH3:1])[CH3:18])[CH2:14][CH2:13]2)[CH3:16])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 52377364-Bromophenyl chloroformateHCID 178484858HCID 178484858, compound

Product 1

HCID 178483793HCID 178483793, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 150 mg (0.55 mmol) of trans-N-(2-dimethylamino-ethyl)-N-methyl-2-(4-methylamino-cyclohexyloxy)-acetamide in 4 mL of CH2Cl2 were added 0.14 mL (0.8 mmol, 1.5 eq) of N,N-diisopropylethylamine followed by 0.08 mL (0.58 mmol, 1.1 eq) of 4-bromophenyl chloroformate. The mixture was stirred at RT for 2 h, and the solution was added to a mixture of NaHCO3 solution and CH2Cl2. The phases were separated and the inorganic one was extracted with CH2Cl2. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with CH2Cl2:MeOH 9:1 yielded 174 mg (67%) of trans-(4-{[(2-dimethylamino-ethyl)-methyl-carbamoyl]-methoxy}-cyclohexyl)-methyl-carbamic acid 4-bromo-phenyl ester as colorless oil, MS: 470 (MH+,1Br).

Workup

  1. customThe phases were separated
  2. extractionthe inorganic one was extracted with CH2Cl2
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-1c2f8a55dd384dc9a38a843f516e1e89
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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