Methanesulfonyl chloride → (R)-3-chloro-1-(4-pyrrolidinophenethyl)piperidine

HRID 2251888Notes

Reaction equation

HRID 2251888 reaction equation
O[CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C.CS([Cl:34])(=O)=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:34][C@@H:6]1[CH2:7][CH2:2][CH2:3][N:4]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[CH:14][CH:15]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 69198126(R)-2-hydroxymethyl-1-(4-pyrrolidinophenethyl)pyrrolidine

Product 1

HCID 69201531(R)-3-chloro-1-(4-pyrrolidinophenethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-2-Hydroxymethyl-1-(4-pyrrolidinophenethyl)pyrrolidine (4.96 g, 19.1 mmol) was dissolved in 70 ml of dichloromethane. 3.21 g (24.8 mmol) of diisopropylethylamine and 2.84 g (24.8 mmol) of methanesulfonyl chloride were added to the obtained solution under stirring under cooling with ice. They were stirred under cooling with ice for 1 hour and then at room temperature for 2 hours. The reaction mixture was distributed into dichloromethane and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with hexane and ethyl acetate (3:1) as the eluent, suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (R)-3-chloro-1-(4-pyrrolidinophenethyl)piperidine in the form of a light yellow solid (3.23 g, 61%).

Workup

  1. temperatureunder cooling with ice
  2. stirringThey were stirred
  3. temperatureunder cooling with ice for 1 hour
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washAfter the elution with hexane and ethyl acetate (3:1) as the eluent, suitable fractions
  7. customwere collected
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-08b17510a4e9486c934d8deba0889dcf
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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