Water → 1-Benzyl-3-(5-chloro-2-methoxyphenyl)pyrrolidine

HRID 1743756Notes

Reaction equation

HRID 1743756 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH:8]([CH2:12][C:13](O)=O)[C:9](O)=O)[CH:7]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1(C)C(C)=CC=CC=1>[CH2:18]([N:25]1[CH2:13][CH2:12][CH:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])[CH2:9]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 222365742-(5-Chloro-2-methoxyphenyl)succinic acid

Product 1

HCID 222365641-Benzyl-3-(5-chloro-2-methoxyphenyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.0 g of 2-(5-chloro-2-methoxyphenyl)succinic acid is suspended in 50 ml of xylene, 0.47 ml of benzylamine is added and the mixture refluxed for 8 hours with separation of water. The solvent is evaporated and the residue taken up in ethylacetate and extracted with 2N HCl, followed by 2N NaOH and aqueous NaCl. The organic layer is dried, filtered and the solvent evaporated. The dried residue is purified by flash chromatography using t-butylmethylether/hexane 1/1 providing the amorphous product: MS (EI): M+=329; NMR (DMSO): 2.65 (1H, dd), 3.1 (1H, dd), 3.45 (3H, s), 4.2 (1H, dd), 4.6 (2H, s), 7.0 (1H, d), 7.25-7.4 (7H, m).

Workup

  1. customThe solvent is evaporated
  2. extractionextracted with 2N HCl
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe dried residue is purified by flash chromatography

Sources & evidence

ORD record
ord-f82494d4ed1c4757a5f2ed14f633490f
Source dataset
uspto-grants-2006_03
Patent number
US07012085B2

Reaction notes

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