Triethylamine → (R)-3-chloro-1-(3-methoxyphenethyl)homopiperidine

HRID 1859425Notes

Reaction equation

HRID 1859425 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][CH:14]=[C:13]([O:17][CH3:18])[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:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69900408(R)-2-Hydroxymethyl-1-(3-methoxyphenethyl)piperidine

Product 1

HCID 22975049(R)-3-chloro-1-(3-methoxyphenethyl)homopiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-2-Hydroxymethyl-1-(3-methoxyphenethyl)piperidine (322 mg, 1.28 mmol) was dissolved in 10 ml of dichloromethane. Triethylamine (170 mg, 1.68 mmol) and methanesulfonyl chloride (192 mg, 1.68 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 18 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-(3-methoxyphenethyl)homopiperidine in the form of a light yellow oil (182 mg, 53%).

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-a59cb0c3e7844591a679b7eb3c31022f
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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