Isopropylamine → 4-(4-methoxyphenyl)-N-(1-methylethyl)butylamine

HRID 2417991Notes

Reaction equation

HRID 2417991 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12]Br)=[CH:5][CH:4]=1.[CH:14]([NH2:17])([CH3:16])[CH3:15]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][NH:17][CH:14]([CH3:16])[CH3:15])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 5781911-(4-Bromobutyl)-4-methoxybenzene

Product 1

HCID 204469294-(4-methoxyphenyl)-N-(1-methylethyl)butylamine

Conditions

Temperature
100 °C

Procedure

A solution of (50 ml) isopropylamine and 4-(4-methoxyphenyl)butyl bromide (13.7 g) in a glass lined vessel was heated under nitrogen (initial pressure, 500 psi) for 12 hours at 100° C. The solvent was removed in vacuo and water (200 ml) was added to the residue. The solution was acidified with concentrated hydrochloric acid and the solution was extracted with ether. The extract was dried over potassium carbonate and the solvent was removed in vacuo. The residue, 4-(4-methoxyphenyl)-N-(1-methylethyl)butylamine, weighed 9.3 g (75%). The identity and purity (94.8%) of the product was determined by mass spectrum and gas chromatography.

Workup

  1. customThe solvent was removed in vacuo and water (200 ml)
  2. additionwas added to the residue
  3. extractionthe solution was extracted with ether
  4. dry with materialThe extract was dried over potassium carbonate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-70a8b85604b7449ebbe788cd8acdafb8
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

Loading…