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

HRID 903424노트

반응식

HRID 903424 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 80711,2-Dimethoxyethane용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ebd1c9ca8684c6ab92b724d97ae688f
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04227014

반응 노트

불러오는 중…