Triethylamine → N-(3-bromopropyl)-2-(4-tetradecenylamino)benzamide

HRID 325572Notes

Reaction equation

HRID 325572 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl.[CH2:8]([NH:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26])[CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.COCCOC>[Br:2][CH2:3][CH2:4][CH2:5][NH:6][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[NH:22][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 787013-Bromopropylamine hydrobromideHCID 737080852-(4-Tetradecenylamino)benzoyl chloride hydrochloride

Product 1

HCID 54261894N-(3-bromopropyl)-2-(4-tetradecenylamino)benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a slurry of 21.80 g. of 3-bromopropylamine hydrobromide in 200 ml. of glyme at 3° C. is added a solution of 23.9 g. of 2-(4-tetradecenylamino)benzoyl chloride hydrochloride in 65 ml. of glyme, concurrently with 26 ml. of triethylamine diluted to 39 ml. with 1,2-dimethoxyethane. The solution is warmed to reflux and 0.2 g. of 4-dimethylaminopyridine is added. The solution is heated for four hours and cooled overnight. The solid is removed and the mother liquor diluted with 200 ml. of water to yield a solid which is crystallized from cyclohexane and recrystallized from acetonitrile to yield the product.

Workup

  1. temperatureThe solution is warmed
  2. temperatureto reflux
  3. temperatureThe solution is heated for four hours
  4. temperaturecooled overnight
  5. customThe solid is removed
  6. additionthe mother liquor diluted with 200 ml
  7. customof water to yield a solid which
  8. customis crystallized from cyclohexane
  9. customrecrystallized from acetonitrile
  10. customto yield the product

Sources & evidence

ORD record
ord-edc8f3b061ed4b3995aa791cd60751cd
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Reaction notes

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