Isoamylamine → HCID 57937846, compound

HRID 1435061Notes

Reaction equation

HRID 1435061 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH3:10].[CH2:11]([NH2:16])[CH2:12][CH:13]([CH3:15])[CH3:14].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:16][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 4311764Sodium borohydrideHCID 109215214-Bromo-3-methylbenzaldehyde

Product 1

HCID 57937846HCID 57937846, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-bromo-3-methyl-benzaldehyde (2a: 10.20 g, 51.2 mmol) was dissolved in methanol (150 ml) before adding isoamyl amine (6.75 g, 77 mmol). After stirring overnight at room temperature, sodium borohydride (5.9 g, 154 mmol) was added. After stirring for 1 hour at room temperature, the reaction was quenched using concentrated (37%) hydrochloric acid and the volatiles were removed with a rotary evaporator under reduced pressure. The resulting residue was made basic with a 2 N aqueous sodium hydroxide solution and extracted twice with ethyl acetate. The combined organics were washed with a saturated aqueous sodium bicarbonate solution and dried over sodium sulfate, filtered and concentrated under reduced pressure to provide 13.7 g of the title compound (I-2b).

Workup

  1. stirringAfter stirring for 1 hour at room temperature
  2. customthe reaction was quenched
  3. concentrationusing concentrated (37%) hydrochloric acid
  4. customthe volatiles were removed with a rotary evaporator under reduced pressure
  5. extractionextracted twice with ethyl acetate
  6. washThe combined organics were washed with a saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b43a30031f6444abd60a872969ac5fc
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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