Aluminium lithium hydride → 4-Bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzylamine

HRID 1859206Notes

Reaction equation

HRID 1859206 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 221232864-Bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzonitrile

Product 1

HCID 221232774-Bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzylamineYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The crude 4-bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzonitrile (3.04 g) dissolved in dry tetrahydrofuran (50 mL) was dropped to an ice-cold slurry of lithium aluminium hydride 4.16 g, 0.11 mmol) in dry tetrahydrofuran (50 mL). The mixture was stirred for 1 h at ambient temperature, and then heated at reflux for another hour. The flask was cooled on ice, and the reaction mixture quenched with water (4.2 mL) followed by 15% NaOH(aq) (4.2 mL). Additional water (12.6 mL) was added and the mixture stirred at ambient temperature for 1 h. The white precipitate was filtered and washed with tetrahydrofuran. Evaporation afforded crude 4-bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzylamine (3.20 g) as a yellow oil. This was stirred together with ethyl trifluoroacetate (2.5 ml, 20.9 mmol) in dry methylene chloride (50 mL) for 17 h at room temperature. Evaporation followed by chromatography (ethyl acetate/heptane: 25/75) gave the sub-title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for another hour
  3. temperatureThe flask was cooled on ice
  4. customthe reaction mixture quenched with water (4.2 mL)
  5. additionAdditional water (12.6 mL) was added
  6. stirringthe mixture stirred at ambient temperature for 1 h
  7. filtrationThe white precipitate was filtered
  8. washwashed with tetrahydrofuran
  9. customEvaporation

Sources & evidence

ORD record
ord-5ff9e5d003ab4e2c8163f837df9e758e
Source dataset
uspto-grants-2000_11
Patent number
US06153641

Reaction notes

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