Phenethylamine → HCID 131711409, compound

HRID 1733503Notes

Reaction equation

HRID 1733503 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 (H2O) 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 (H2O) giving 4.45 g
  7. customAn aliquot (0.5 g.) was recrystallized from 29 ml

Sources & evidence

ORD record
ord-e773c736ba1648c3bc596315f36d1267
Source dataset
uspto-grants-1980_12
Patent number
US04242273

Reaction notes

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