Potassium Carbonate → 6-[4-(3-Phenylpropyl)-1,4diazepan-1-yl]-1-(4,4,4-trifluorobutyl)benzo [cd]indol-2(1H)-one

HRID 433099Notes

Reaction equation

HRID 433099 reaction equation
[N:1]1([C:8]2[C:9]3[C:10]4[C:14](=[CH:15][CH:16]=2)[N:13]([CH2:17][CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:12](=[O:24])[C:11]=4[CH:25]=[CH:26][CH:27]=3)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:9]1([CH2:27][CH2:26][CH2:25][N:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:8]3[C:9]4[C:10]5[C:14](=[CH:15][CH:16]=3)[N:13]([CH2:17][CH2:18][CH2:19][C:20]([F:21])([F:22])[F:23])[C:12](=[O:24])[C:11]=5[CH:25]=[CH:26][CH:27]=4)[CH2:2][CH2:3]2)[CH:10]=[CH:14][CH:15]=[CH:16][CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 121138336-(1,4-Diazepan-1-yl)-1-(4,4,4-trifluorobutyl)-benzo[cd]indol-2(1H)-one

Product 1

HCID 104134536-[4-(3-Phenylpropyl)-1,4diazepan-1-yl]-1-(4,4,4-trifluorobutyl)benzo [cd]indol-2(1H)-oneYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude product from step 3 was dissolved in 30 ml acetonitrile and distributed into 30 vials (2 ml size) preloaded with potassium carbonate (300 mg, 2.3 mmol). Next, 1-bromo-3-phenylporpane (135 μl, 0.135 mmol) was then added and the mixture was shaked on a robital shaker for 18 hours at room temperature. The reaction was then worked up by pipetting out most of the solution and running through a prep HPLC using the Gilson system. The product (62 mg, 54%) was obtained by stripping off the solvent on a speed-vac.

Workup

  1. additionNext, 1-bromo-3-phenylporpane (135 μl, 0.135 mmol) was then added

Sources & evidence

ORD record
ord-50a9bceb8b25420b8b183d11a0591340
Source dataset
uspto-grants-2003_12
Patent number
US06667303B1

Reaction notes

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