Sodium Carbonate → HCID 70064159, compound

HRID 233800Notes

Reaction equation

HRID 233800 reaction equation
[CH3:1][CH:2]1[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13]C)[CH:8]=2)[CH2:4][N:3]1[CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>Br>[CH3:1][C@H:2]1[CH2:6][C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=2)[CH2:4][N:3]1[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 23358044HCID 23358044, compound

Product 1

HCID 70064159HCID 70064159, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-Methyl-4-(3-methoxyphenyl)-N-n-propylpyrrolidine (cis and trans mixture 85: 15, 920 mg, 3.95 mmol) was dissolved in 47% hydrobromic acid (20 mL) and heated at reflux temperature for 1.5 hours. The mixture was made alkaline by the addition of 10% sodium carbonate (75 mL) and the product extracted with diethyl ether and ethyl acetate (1:1,3×20 mL). Drying (MgSO4) afforded 840 mg of the crude product as a white solid. Chromatography on a SiO2HPLC column yielded 601 mg of the title compound.: m.p. 123°-24° C.; MS (EI) m/e calc'd for C14H21NO: 219.162, found 219.163; 219.15 (10, M+), 204.05 (47), 191.05 (14), 190.05 (100), 161.05 (6), 133.05 (6), 106.95 (8), 90.95 (6), 84.05 (12).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1.5 hours
  3. extractionthe product extracted with diethyl ether and ethyl acetate (1:1,3×20 mL)
  4. dry with materialDrying (MgSO4)
  5. customafforded 840 mg of the crude product as a white solid

Sources & evidence

ORD record
ord-0bac920b316f4e419177ff71b559bba0
Source dataset
uspto-grants-1997_01
Patent number
US05594024

Reaction notes

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