Triethylamine → (r)-3-Chloro-1-(4-methoxyphenethyl)homopiperidine

HRID 1859421Notes

Reaction equation

HRID 1859421 reaction equation
O[CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.C(N(CC)CC)C.CS([Cl:30])(=O)=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:30][C@@H:6]1[CH2:7][CH2:8][CH2:2][CH2:3][N:4]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69902512(R)-2-hydroxymethyl-1-(4-methoxyphenethyl)piperidine

Product 1

HCID 22975052(r)-3-Chloro-1-(4-methoxyphenethyl)homopiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-2-Hydroxymethyl-1-(4-methoxyphenethyl)piperidine (617 mg) was dissolved in 10 ml of dichloromethane. Triethylamine (0.30 g, 2.7 mmol) and methanesulfonyl chloride (0.30 g, 2.6 mmol) were added to the obtained solution under stirring under cooling on ice. They were stirred under cooling on ice for 1 hour and then at room temperature for 4 hours. The reaction liquid was distributed in dichloromethane and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain (R)-3-chloro-1-(4-methoxy-phenethyl)homopiperidine in the form of a light yellow oil (632 mg, 97%).

Workup

  1. temperatureunder cooling on ice
  2. stirringThey were stirred
  3. temperatureunder cooling on ice for 1 hour
  4. customThe reaction liquid
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8a1aef8e8ac149ddbb3381769d74e630
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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