Formic Acid → 2-Methyl-1-phenylpropan-1-amine

HRID 2425998Notes

Reaction equation

HRID 2425998 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)[CH:2]([CH3:4])[CH3:3].C(O)=O.C(OCC)C.C([NH2:22])=O>O>[CH3:3][CH:2]([CH3:4])[CH:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH2:22]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 713FormamideHCID 3283Diethyl EtherHCID 69144Isobutyrophenone

Product 1

HCID 49628752-Methyl-1-phenylpropan-1-amineYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of isobutyrophenone (5.1 mL, 33.7 mmol) and formic acid (1.3 mL, 33.7 mmol) in formamide was stirred at 165-180° C. for 20 h. The mixture was cooled, diluted with water, and extracted with benzene. The benzene was concentrated down and the residue was boiled in 3 M HCl (10 mL) for 48 h. The cooled reaction mixture was added to diethyl ether and extracted with water. The combined water extracts were basified with 20% NaOH, and extracted with dichloromethane. The combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to yield 3.09 g (61%) of the desired amine: 1H NMR (400 MHz, CD3OD): δ 7.33-7.23 (m, 4H), 7.22-7.20 (m, 1H), 3.49 (d, 1H), 1.87 (m, 1H), 1.00 (d, 3H), 0.73 (d, 3H). MS (ESI) m/z: Calculated: 149.12; Observed: 149.9 (M++1).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with benzene
  3. concentrationThe benzene was concentrated down
  4. customThe cooled reaction mixture
  5. extractionextracted with water
  6. extractionextracted with dichloromethane
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee7b8a68f07743b8aaa6ae7195e4dbdf
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

Loading…