Triethylamine → 4-[(8-cyclohexyloctyl)amino]-N-3-bromopropylbenzamide

HRID 903424Notes

Reaction equation

HRID 903424 reaction equation
[BrH:1].Br[CH:3]([CH3:6])[CH2:4][NH2:5].Cl.[CH:8]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]2[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(COC)OC>[CH:8]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([NH:5][CH2:4][CH2:3][CH2:6][Br:1])=[O:28])=[CH:25][CH:24]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 125707032-Bromopropan-1-amine hydrobromideHCID 20475769p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochloride

Product 1

HCID 204757754-[(8-cyclohexyloctyl)amino]-N-3-bromopropylbenzamide

Reagents, catalysts & solvents 2

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

Procedure

To a slurry of 21.80 g. of 2-bromopropylamine hydrobromide in 200 ml. of glyme at 3° C. is added a solution of 23.96 g. of 4-(8-cyclohexyloctylamino)benzoyl chloride hydrochloride in 65 ml. of glyme, concurrently with 26 ml. of triethylamine diluted to 39 ml. with glyme. 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 by filtration and the filtrate diluted with 200 ml. of water. The precipitate is collected and crystallized from cyclohexane. The solid is 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 by filtration
  6. additionthe filtrate diluted with 200 ml
  7. customThe precipitate is collected
  8. customcrystallized from cyclohexane
  9. customThe solid is recrystallized from acetonitrile
  10. customto yield the product

Sources & evidence

ORD record
ord-8ebd1c9ca8684c6ab92b724d97ae688f
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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