Acetic Acid → [1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamine

HRID 2114334Notes

Reaction equation

HRID 2114334 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.CN.[BH3-][C:19]#[N:20].[Na+].C(O)(=O)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:20][CH3:19])[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 21383095HCID 21383095, compound

Product 1

HCID 57425537[1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethanone (4.45 g, 16.6 mmol) and methyl amine (33 mL, 66.4 mmol of 2 M solution in THF) were dissolved in 75 mL THF and maintained for 15 minutes at room temperature. NaBH3CN (3.13 g, 49.8 mmol) was added and the reaction mixture was treated with 1 mL acetic acid and stirred at room temperature for 4 days. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.7 g (99%) of the title compound as a yellow oil. MS (ES) m/e 284 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 100 mL of EtOAc
  3. washwashed with sodium bicarbonate (100 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7dcb942ef37447297279b9769af5920
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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