Hydrochloric Acid → HCID 66785340, compound

HRID 1095431Notes

Reaction equation

HRID 1095431 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=3)[NH:21][CH:20]=2)=[O:18])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:29]>ClCCl>[ClH:29].[ClH:29].[F:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59799435HCID 59799435, compound

Product 1

HCID 66785340HCID 66785340, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 4-[4-(5-fluoro-1H-indol-3-yl)-4-oxobutyl]-piperazine-1-carboxylic acid tert-butyl ester (3.85 g, 9.88 mmol) in dichloromethane was added hydrochloric acid (dissolved in dioxane: 4.94 ml, 4M solution, 19.8 mmol HCl) and the resulting mixture was reacted at room temperature for 4 hours. The reaction mixture was thoroughly concentrated in vacuo to give 1-(5-fluoro-1H-indol-3-yl)-4-(piperazin-1-yl)butan-1-one dihydrochloride (3.20 g). Some characteristic 1H-NMR signals from 1-(5-fluoro-1H-indol-3-yl)-4-(piperazin-1-yl)butan-1-one dihydrochloride are: (400 MHz, DMSO-d6) δ 2.07 (quintet, J=7, 2H), 3.03 (t, J=7, 2H), 7.08 (dt, J˜9 and 3, 1H), 7.50 (dd, J˜9 and 4, 1H), 7.85 (dd, j˜9 and 3, 1H), 8.43 (d, J˜3, 1H), 12.21 (br s, 1H).

Workup

  1. customthe resulting mixture was reacted at room temperature for 4 hours
  2. concentrationThe reaction mixture was thoroughly concentrated in vacuo

Sources & evidence

ORD record
ord-d1b33bfe361c4b56b9e562d9ded1a970
Source dataset
uspto-grants-2012_03
Patent number
US08138174B2

Reaction notes

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