Propargyl bromide → N-cyclopentylmethyl-N-propargyl-9-anthracenemethylamine

HRID 1678897

반응식

HRID 1678897 반응식
[CH:1]1([CH2:6][NH:7][CH2:8][C:9]2[C:10]3[C:15]([CH:16]=[C:17]4[C:22]=2[CH:21]=[CH:20][CH:19]=[CH:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:23](Br)[C:24]#[CH:25].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH:1]1([CH2:6][N:7]([CH2:25][C:24]#[CH:23])[CH2:8][C:9]2[C:10]3[C:15]([CH:16]=[C:17]4[C:22]=2[CH:21]=[CH:20][CH:19]=[CH:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 20353249N-cyclopentylmethyl-9-anthracenemethylamine

생성물 1

HCID 20353224N-cyclopentylmethyl-N-propargyl-9-anthracenemethylamine수율 88.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 63.5 g of N-cyclopentylmethyl-9-anthracenemethylamine, 50 g of propargyl bromide, 200 ml of methylene chloride and 200 ml of 10% aqueous, potassium carbonate solution is stirred vigorously under nitrogen for two hours. The layers are separated and the aqueous layer is extracted once with methylene chloride. Removal of the solvent from the dried extract gives 63.5 g of N-cyclopentylmethyl-N-propargyl-9-anthracenemethylamine as an oil; nmr spectrum: τ 2.3-3.0 (m, 9); 5.5 (s, 2) 6.8 (d, 2.5Hz, 2); 7.5 (m, 2); 7.7 (t, 2.5Hz, 1) and 7.5-9.2 (m, 9). This product is cyclized by heating under reflux in 200 ml toluene for 1.25 hours. Removal of the solvent and crystallization of the residue from 150 ml of isopropyl alcohol gives 44.4 g of 2-cyclopentylmethyl-1,2,3,5-tetrahydro-5,9b-o-benzenobenz[e]isoindole, identical by infrared and nmr spectroscopy with the sample prepared by acylation of 1,2,3,5-tetrahydro-5,9b-o-benzenobenz[e]isoindole with cyclopentanecarbonyl chloride followed by reduction.

후처리

  1. customThe layers are separated
  2. extractionthe aqueous layer is extracted once with methylene chloride
  3. customRemoval of the solvent from the dried
  4. extractionextract

출처 및 근거

ORD 기록
ord-3ef1ea1342914a6594f8e71352ef15da
출처 데이터셋
uspto-grants-1978_03
특허 번호
US04077977

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