Ether hydrochloride → HCID 67372870, compound

HRID 1677813Notes

Reaction equation

HRID 1677813 reaction equation
[C:1]1([S:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:25].CCOCC>CCOC(C)=O>[ClH:25].[C:1]1([S:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 67371141HCID 67371141, compound

Product 1

HCID 67372870HCID 67372870, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Treat 1H-indole-2-carboxylic acid 3 (X═H, 1.0 mg, 6.21 mmol) with N-(tert-butoxycarbonyl)piperazine (1.10 equiv., 1.3 g, 6.83 mmol) as described in General Synthetic Procedure VIa to afford 4-(1H-indole-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester 8 (X═H, R4=piperazin-4-yl-1-carboxylic acid tert-butyl ester; 2.0 g, 99%) as a white solid, mp 205-206° C. 1H NMR (DMSO-d6) δ 11.6 (brs, 1H), 7.6 (d, 1H), 7.4 (d, 1H), 7.2 (t, 1H), 7.1 (t, 1H0, 6.8 (s, 1H), 3.8-3.7 (m, 4H), 3.5-3.4 (m, 4H), 1.4 (s, 9H); m/z=330 (M+1). Treat 4-(1H-indole-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (329 g, 1.0 mmol) with phenyldisulfide (283 mg, 1.3 equiv., 1.3 mmol) as described in General Synthetic Procedure VIIa and then treat with trifluoroacetic acid (4 mL) in HOAc, to remove the Boc protecting group, to afford (3-phenylsulfanyl-1H-indol-2-yl)-piperazin-1-yl-methanone. Dissolve (3-phenylsulfanyl-1H-indol-2-yl)-piperazin-1-yl-methanone in EtOAc and treat with 1N HCl/Et2O to provide the title compound Iae (103 mg, 29%) as a tan solid, mp 240° C. (dec); m/z=338 (M+1).

Sources & evidence

ORD record
ord-82bf6deb03b0493ebcd90d319a6d2545
Source dataset
uspto-grants-2011_08
Patent number
US08008340B2

Reaction notes

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