Hydrochloric Acid → HCID 86596814, compound

HRID 751415Notes

Reaction equation

HRID 751415 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2[Cl:22])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.Cl>>[ClH:22].[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 86035946HCID 86035946, compound

Product 1

HCID 86596814HCID 86596814, compoundYield 46%

Procedure

1-(4-Butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde is reacted with piperazine as described in Step 2 of Example 29 and subsequently treated with hydrochloric acid as described in Example 44 to afford 1-(4-butylphenyl)-2-(piperazin-1-yl)-1H-indole-3-carboxaldehyde hydrochloride (46% yield) as a cream solid. ESI/MS 362 (M+H); RT=3.02 min; NMR 10.13 (1H, s); 8.12 (1H, d, J=9 Hz); 7.48 (4H, s); 7.21 (2H, m); 6.94 (1H, d, J=9 Hz); 3.41 (4H, br m); 2.97 (4H, br m); 2.74 (2H, t); 1.64 (2H, p); 1.37 (2H, m); 0.97 (3H, t).

Sources & evidence

ORD record
ord-2902048a7e354ffc9e0d6863c973b30f
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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