Triethylamine → HCID 13478148, compound

HRID 2350913Notes

Reaction equation

HRID 2350913 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[F:13][C:14]([F:40])([F:39])[C:15]1[CH:16]=[C:17]([C:25]#[C:26][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([C:34]([CH3:38])([CH3:37])[CH2:35][OH:36])[CH2:30][CH2:29]2)[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1>O1CCCC1>[F:22][C:21]([F:24])([F:23])[C:19]1[CH:18]=[C:17]([C:25]#[C:26][CH2:27][N:28]2[CH2:29][CH2:30][CH:31]([C:34]([CH3:37])([CH3:38])[CH2:35][O:36][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:32][CH2:33]2)[CH:16]=[C:15]([C:14]([F:39])([F:13])[F:40])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13478142HCID 13478142, compound

Product 1

HCID 13478148HCID 13478148, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.75 g), followed by methylsulphonyl chloride (0.85 g) were added to a solution of 1-(3,5-bistrifluoromethylphenyl)-3-[4-(1,1-dimethyl-2-hydroxyethyl)piperidino]-prop-1-yne (3.0 g) in tetrahydrofuran (50 ml). After stirring for 5 hours, the precipitate of triethylamine hydrochloride was filtered off, and the filtrate was evaporated in vacuo to give a brown gum. This gum was purified by medium pressure chromatography using a mixture of dichloromethane and ethyl acetate (85:15) as eluent to give 1-(3,5-bistrifluoromethylphenyl)-3-[4-(1,1-dimethyl-2-methylsulphonyloxyethyl)piperidino]prop-1-yne (2.4 g) as a colourless gum.

Workup

  1. filtrationthe precipitate of triethylamine hydrochloride was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customto give a brown gum
  4. customThis gum was purified by medium pressure chromatography
  5. additiona mixture of dichloromethane and ethyl acetate (85:15) as eluent

Sources & evidence

ORD record
ord-a9742078249b47029f1a4ff26615121e
Source dataset
uspto-grants-1989_10
Patent number
US04871748

Reaction notes

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