Acetonitrile → HCID 67819886, compound

HRID 484164Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:22][C@@H:6]2[CH2:7][N:8]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]3[CH:10]=[CH:11][C:12]([Br:13])=[C:4]([C:5]=32)[CH2:3]1.[CH2:23](I)[CH2:24][CH3:25].[C:27]([O-])([O-])=O.[K+].[K+].[CH3:33][C:34]#N>>[C:14]([N:8]1[C:9]2[CH:10]=[CH:11][C:12]([Br:13])=[C:4]3[CH2:3][C@@H:2]([N:1]([CH2:27][CH2:34][CH3:33])[CH2:23][CH2:24][CH3:25])[CH2:22][C@@H:6]([C:5]=23)[CH2:7]1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 11430Potassium Carbonate

HCID 336431-Iodopropane

HCID 57294480HCID 57294480, compound

Product 1

HCID 67819886HCID 67819886, compound

Procedure

Using the procedure of Example 4D, the reaction of (2aS,4S)-4-amino-1-benzoyl-6-bromo-1,2,2a,3,4,5-hexahydrobenz[cd]indole(5.4 g, 0.015 mol) with n-propyliodide (10.2 g, 0.06 mol) in the presence of K2CO3 (8.28 g, 0.06 mol) in 200 ml of CH3CN gave, after chromatography, 3.1 g of product.

Workup

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Sources & evidence

ORD record: ord-91c80fd2f58e4973b475b378cb971aa8
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05229410

Reaction notes

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