Isoamylamine → HCID 57937850, compound

HRID 1435082Notes

Reaction equation

HRID 1435082 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[CH:11][C:10]=2[CH3:18])=[CH:5][CH:4]=1)=O.[CH2:19]([NH2:24])[CH2:20][CH:21]([CH3:23])[CH3:22].[BH4-].[Na+]>CO>[CH3:18][C:10]1[CH:11]=[C:12]([C:15]([NH2:17])=[O:16])[CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:1][NH:24][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 4311764Sodium borohydrideHCID 57937848HCID 57937848, compound

Product 1

HCID 57937850HCID 57937850, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4′-Formyl-2-methylbiphenyl-4-carboxamide (I-4a: 4.3 g, 18.0 mmol) and isoamylamine (36.2 mg, 0.425 mmol) were combined in methanol (100 ml). After 12 hours, the reaction mixture was treated with sodium borohydride (2.10 g, 53.9 mmol). After 1 hour, the reaction mixture was treated with concentrated (37%) aqueous hydrochloric acid solution and the volatiles were removed under reduced pressure. The residue was taken up in 2N sodium hydroxide and extracted with ethyl acetate (2 times). The combined organic phases were washed with a saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound (E4-01).

Workup

  1. waitAfter 1 hour
  2. additionthe reaction mixture was treated
  3. concentrationwith concentrated (37%) aqueous hydrochloric acid solution
  4. customthe volatiles were removed under reduced pressure
  5. extractionextracted with ethyl acetate (2 times)
  6. washThe combined organic phases 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-3b91d6089ddf4879903e9f334d88f59a
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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