Triethylamine → HCID 15480809, compound

HRID 1058608Notes

Reaction equation

HRID 1058608 reaction equation
[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>O1CCCC1>[CH3:35][S:36]([O:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12851305HCID 12851305, compound

Product 1

HCID 15480809HCID 15480809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 84.0 g of N-triphenylmethyl-4-piperidinemethanol and 36.2 ml of triethylamine in 420 ml of dried tetrahydrofuran, 18.3 ml of methanesulfonyl chloride was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 5.5 hours. The reaction mixture was added with waiter and extracted with diethyl ether. The extract was washed successively with water and saturated brine, and dried, and then the solvent was evaporated. The resulting residue was added with a mixture of isopropanol and methanol, and the precipitated crystals were collected by filtration and washed with methanol to give 90.4 g of colorless crystals. Recrystallization from a mixture of methylene chloride and methanol gave colorless prisms having the melting point of from 129.5 to 134° C.

Workup

  1. temperaturecooling
  2. additionThe reaction mixture was added with waiter
  3. extractionextracted with diethyl ether
  4. washThe extract was washed successively with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated
  7. additionThe resulting residue was added with a mixture of isopropanol and methanol
  8. filtrationthe precipitated crystals were collected by filtration
  9. washwashed with methanol

Sources & evidence

ORD record
ord-ffacc612325a45fab6b359168d0ed0bc
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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