Aluminium lithium hydride → N-({2-chloro-5-[3-(methyloxy)propyl]phenyl}methyl)cyclopropanamine

HRID 1715393Notes

Reaction equation

HRID 1715393 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:16][C:9]=1[C:10]([NH:12][CH:13]1[CH2:15][CH2:14]1)=O>C1COCC1>[Cl:7][C:8]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:16][C:9]=1[CH2:10][NH:12][CH:13]1[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 685039242-Chloro-N-cyclopropyl-5-(3-methoxy-propyl)-benzamide

Product 1

HCID 57956085N-({2-chloro-5-[3-(methyloxy)propyl]phenyl}methyl)cyclopropanamineYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (5.70 g, 151 mmol) was added in portions to a sol. of 2-chloro-N-cyclopropyl-5-(3-methoxy-propyl)-benzamide (10 g, 37.7 mmol) in THF (230 mL) at 0° C. The ice bath was removed, and the mixture was heated to reflux for 4 h. The mixture was allowed to cool to rt, and was cooled to 0° C. Water (7.5 mL), aq. 15% NaOH (17 mL), and water (5.7 mL) were carefully added. The mixture was filtered, and the precipitate was washed with EtOAc. The filtrate was evaporated under reduced pressure. The residue was diluted with EtOAc, and the resulting mixture was washed with water, and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:4→1:3→1:2) yielded the title compound (5.60 g, 59%). LC-MS: tR=0.86 min; ES+: 254.19.

Workup

  1. customThe ice bath was removed
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 4 h
  4. temperaturewas cooled to 0° C
  5. additionWater (7.5 mL), aq. 15% NaOH (17 mL), and water (5.7 mL) were carefully added
  6. filtrationThe mixture was filtered
  7. washthe precipitate was washed with EtOAc
  8. customThe filtrate was evaporated under reduced pressure
  9. additionThe residue was diluted with EtOAc
  10. washthe resulting mixture was washed with water, and brine
  11. dry with materiallayer was dried over MgSO4
  12. filtrationfiltered
  13. customthe solvents were removed under reduced pressure
  14. customPurification of the residue by FC (EtOAc/heptane 1:4→1:3→1:2)

Sources & evidence

ORD record
ord-532f7c07c5204477a7f66144965826b5
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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