Carbon tetrabromide → 4-(3-(2-Bromoethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine

HRID 1095599ノート

反応式

HRID 1095599 の反応式
[CH3:1][N:2]([CH3:27])[C:3]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19]O)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1.[Br:28]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:28][CH2:19][CH2:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[CH:6]1[CH2:7][CH2:8][C:3]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([N:2]([CH3:27])[CH3:1])[CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 236585632-(2-(4-(Dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethanol

生成物 1

HCID 667836244-(3-(2-Bromoethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine収率 52.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-[2-(4-Dimethylamino-4-phenyl-cyclohexyl)-1H-indol-3-yl]-ethanol (Example 219, 3.20 g, 8.8 mmol) was dissolved in abs. CH2Cl2 (50 ml) at RT and tetrabromomethane (4.39 g, 13.2 mmol) was added. Triphenylphosphine (3.61 g, 12.6 mmol) was then added at RT. The solution was stirred at RT for 2.5 h and then concentrated i. vac. Flash chromatography of the residue with 300 g of silica gel and ethyl acetate/ethanol (1:2) gave 1.98 g of contaminated product, 1 N NaOH was added to this and the mixture was extracted three times with CHCl3. The organic phase was dried over Na2SO4 and concentrated i. vac. Yield: 1.57 g (42%)

後処理

  1. concentrationconcentrated i

出典と根拠

ORDレコード
ord-8e41f29428d64667acb1e46ae745fc4c
出典データセット
uspto-grants-2012_03
特許番号
US08138187B2

反応ノート

読み込み中…