Acetic Acid → 2-Methyl-5-phenylpentan-2-amine

HRID 602041Notes

Reaction equation

HRID 602041 reaction equation
[CH3:1][C:2]([NH:13]C(=O)CCl)([CH3:12])[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)(=O)C.NC(N)=S>C(O)C>[CH3:12][C:2]([NH2:13])([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723790Thiourea2×HCID 57470575N-(1,1-dimethyl-4-phenylbutyl)-2-chloroacetamide

Product 1

HCID 122500142-Methyl-5-phenylpentan-2-amineYield 83.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1008 g quantity of N-(1,1-dimethyl-4-phenylbutyl)-2-chloroacetamide (3.98 moles) was dissolved in 8.4 L of ethanol and 1080 mL gl. acetic acid in a 22 L 3-necked, round-bottomed flask equipped with stirrer, thermometer and reflux condenser and 370 g (4.86 moles) of thiourea was added. The reaction was heated to reflux to dissolve the thiourea. A white crystalline precipitate began to form after about two hours of reflux. The reflux was continued for additional 8 h. The reaction mixture was allowed to cool to ambient temperature and was filtered and the filtrate diluted with 8 L of water, extracted with 2×1 L of hexane and neutralized by the addition of 220 mL 50% sodium hydroxide. This caused an oil to form which was separated and the aqueous phase extracted with 2×2 L of ether/hexane. The extracts were combined with the oil and concentrated to give 590 g of reddish oil, LC/MS single peak, m/e 179, NMR (CDCl3) consistent with the desired product, 1,1-Dimethyl-4-phenylbutylamine, 84% crude yield. This material was vacuum distilled to give 518 g of clear oil, bp(1 torr) 71-74°.

Workup

  1. temperaturethermometer and reflux condenser
  2. temperatureThe reaction was heated
  3. temperatureto reflux
  4. customto form after about two hours
  5. temperatureof reflux
  6. filtrationwas filtered
  7. additionthe filtrate diluted with 8 L of water
  8. extractionextracted with 2×1 L of hexane
  9. additionneutralized by the addition of 220 mL 50% sodium hydroxide
  10. customwas separated
  11. extractionthe aqueous phase extracted with 2×2 L of ether/hexane
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-d2518354c06748a39e07d4fd1f28f6ec
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

Loading…