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

HRID 1678897Notes

Reaction equation

HRID 1678897 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ef1ea1342914a6594f8e71352ef15da
Source dataset
uspto-grants-1978_03
Patent number
US04077977

Reaction notes

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