Acetic Anhydride → (+/-)-N-{3-[2,4-bis(methoxymethoxy)phenyl]cyclohexyl}acetamide

HRID 2307137Notes

Reaction equation

HRID 2307137 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[CH3:15][O:16][CH2:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH2:26][O:27][CH3:28])[CH:22]=[CH:21][C:20]=1[CH:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH2:35])[CH2:30]1>ClCCCl>[CH3:15][O:16][CH2:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH2:26][O:27][CH3:28])[CH:22]=[CH:21][C:20]=1[CH:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:8](=[O:10])[CH3:9])[CH2:30]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22337808(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylamine

Product 1

HCID 22337801(+/-)-N-{3-[2,4-bis(methoxymethoxy)phenyl]cyclohexyl}acetamideYield 66%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Triethylamine (15 μl) and acetic anhydride (10 ml) were added to a stirred solution of (±)-3-[2,4-bis(methoxymethoxy)phenyl]cyclohexylamine (29 mg) in anhydrous 1,2-dichloroethane (2 ml) at room temperature. After 0.5 hr, the reaction mixture was partitioned between water (20 ml) and ethyl acetate (50 ml) and the aqueous layer was extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to give the title compound as a solid (22 mg, 66%) and a mixture of diastereoisomers; m/z (ES+) 338 (M+H)+.

Workup

  1. customthe reaction mixture was partitioned between water (20 ml) and ethyl acetate (50 ml)
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×20 ml)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ff5290fcffa646a6a495e9ffd41f3f2e
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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