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

HRID 585674Notes

Reaction equation

HRID 585674 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-1e35e8f4bde14032846cc5db8460686c
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

Loading…