Pyrrolidine → 6-Methoxy-5-(3-pyrrolidin-1-yl-propoxy)-indan-1-one

HRID 1714436Notes

Reaction equation

HRID 1714436 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C:11](=[O:17])[CH2:10][CH2:9]2.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>COCCOC>[CH3:16][O:15][C:14]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2=[O:17])=[CH:7][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 184456765-(3-Bromo-propoxy)-6-methoxy-indan-1-one2×

Product 1

HCID 184458186-Methoxy-5-(3-pyrrolidin-1-yl-propoxy)-indan-1-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-(3-bromo-propoxy)-6-methoxy-indan-1-one (Intermediate J) (2.0 g, 0.0066 mole) and pyrrolidine (1.7 mL, 0.02 mole) was stirred in 50 mL of DME (1,2-Dimethoxyethane) at room temperature overnight under Argon. The reaction was quenched with water (150 mL) and made acidic with 1 N HCl (50 mL). The water solution was washed with ethyl acetate, made basic with 3N NaOH (25 mL) and extracted with ethyl acetate. After washing with brine and drying over sodium sulfate, the solvent was removed in vacuo to yield the title compound. MS m/z 290 (M+H)+.

Workup

  1. customThe reaction was quenched with water (150 mL)
  2. washThe water solution was washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washAfter washing with brine
  5. dry with materialdrying over sodium sulfate
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7de6de5f73b44186af3fb6526f724067
Source dataset
uspto-grants-2010_09
Patent number
US07795440B2

Reaction notes

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