HCID 70574680, compound → 2-[(4-methoxyphenyl)methyl]pyrrolidine

HRID 1278037Notes

Reaction equation

HRID 1278037 reaction equation
C(OC([C:8](=[C:17]1[CH2:21][CH2:20][CH2:19][NH:18]1)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 70574680HCID 70574680, compound

Product 1

HCID 49955292-[(4-methoxyphenyl)methyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Add 80 ml of trifluoroacetic acid to 15 g of the title compound of Example 17 with ice cooling, and stir the produced reaction mixture for 2 hours at room temperature. Distil off the acid under a vacuum. Dissolve the resulting residue in 250 ml of diethyl ether and wash the thus-prepared solution with almost saturated cold sodium carbonate solution (150 ml) and saturated sodium chloride solution. Dry the washed solution over sodium sulfate and distil off the ether before dissolving the residue in 300 ml of ethanol and reducing it with Raney nickel/hydrogen. Concentrate the reduced solution to an oil and distil the oil under a vacuum to obtain 7.5 g (76% of theory) of the title compound (b.p. 88° to 90° at 0.008 mm of Hg).

Workup

  1. customthe produced reaction mixture for 2 hours at room temperature
  2. customDistil off the acid under a vacuum
  3. dissolutionDissolve the resulting residue in 250 ml of diethyl ether
  4. washwash the thus-prepared solution with almost saturated cold sodium carbonate solution (150 ml) and saturated sodium chloride solution
  5. dry with materialDry the washed solution over sodium sulfate
  6. customdistil off the ether
  7. dissolutionbefore dissolving the residue in 300 ml of ethanol
  8. concentrationConcentrate the reduced solution to an oil
  9. customdistil the oil under a vacuum

Sources & evidence

ORD record
ord-61357ace7ab640d18f12334116565d3e
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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