Phenethylamine → HCID 131711409, compound

HRID 1980160Notes

Reaction equation

HRID 1980160 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8]N)=[CH:3][CH:2]=1.C([N:12](CC)CC)C.Cl.[CH2:18]([NH:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>CN(C)C1C=CN=CC=1.C(COC)OC>[CH2:8]([CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:18][NH:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([NH2:12])=[O:40])=[CH:37][CH:36]=1)[CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 131711409HCID 131711409, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a chilled solution of 0.1 g. of 4-dimethylaminopyridine, 5.7 g. of β-phenethylamine and 13 ml. of triethylamine in 55 ml. of dimethoxyethane (glyme) at 10° C. was added 7.4 g. of 4-hexadecylaminobenzoyl chloride hydrochloride in 45 ml. of glyme. The reaction was allowed to warm to room temperature and then refluxed for 2.5 hours. An I.R. showed no acid chloride band at this time. The solution was cooled overnight and filtered giving 9.35 g. of an off-white material. This material was recrystallized from 400 ml. of 90% acetone (H2) giving 4.45 g. and 0.76 g. in two crops (26%). An aliquot (0.5 g.) was recrystallized from 29 ml. of cyclohexane giving 0.44 g. melting point 125°-127° C.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. temperatureThe solution was cooled overnight
  3. filtrationfiltered
  4. customgiving 9.35 g
  5. customThis material was recrystallized from 400 ml
  6. customof 90% acetone (H2) giving 4.45 g
  7. customAn aliquot (0.5 g.) was recrystallized from 29 ml

Sources & evidence

ORD record
ord-999d9636fea44a5b93b26b99134a8c5d
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Reaction notes

Loading…