Triethylamine → (+/-)-N-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanesulfonamide

HRID 585641Notes

Reaction equation

HRID 585641 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH3:13][O:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][O:25][CH3:26])[CH:20]=[CH:19][C:18]=1[CH:27]1[CH2:32][CH2:31][CH2:30][CH:29]([NH2:33])[CH2:28]1>ClCCl>[CH3:13][O:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][O:25][CH3:26])[CH:20]=[CH:19][C:18]=1[CH:27]1[CH2:32][CH2:31][CH2:30][CH:29]([NH:33][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22337808(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylamine

Product 1

HCID 22337797(+/-)-N-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.014 ml) and methanesulfonyl chloride (8 μl) were added to a solution of (±)-3-[2,4-bis(methoxymethoxy)phenyl]cyclohexylamine (27 mg) in dichloromethane (1 ml), and the mixture was stirred under argon at ambient temperature. After 1 hr, the mixture was partitioned between ethyl acetate (20 ml) and sodium hydrogen carbonate (20 ml of a saturated aqueous solution). The aqueous layer was extracted with ethyl acetate (2×20 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to furnish the title compound as an oil and a mixture of diastereoisomers; m/z (ES+) 374 (M+H)+.

Workup

  1. customthe mixture was partitioned between ethyl acetate (20 ml) and sodium hydrogen carbonate (20 ml of a saturated aqueous solution)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×20 ml)
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e12ddaf520614d03b010060dd4b2a789
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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