Hydrochloric Acid → 1-(4-ethylphenyl)-2-(piperazin-1-y)-1H-indole-3-carboxaldehyde hydrochloride

HRID 1678174Notes

Reaction equation

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

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 4837Piperazine

HCID 860359032-Chloro-1-(4-ethylphenyl)-1H-indole-3-carboxaldehyde

Product 1

HCID 112687011-(4-ethylphenyl)-2-(piperazin-1-y)-1H-indole-3-carboxaldehyde hydrochlorideYield 39%

Procedure

2-Chloro-1-(4-ethylphenyl)-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-ethylphenyl)-2-(piperazin-1-y)-1H-indole-3-carboxaldehyde hydrochloride (39% yield) as a cream solid. ESI/MS 334 (M+H); RT=2.67 min; NMR 10.13 (1H, s); 8.11 (1H, d, J=6 Hz); 7.50 (4H, s); 7.24 (2H, m); 6.94 (1H, d, J=6 Hz); 3.42 (4H, m); 2.95 (4H, m); 2.76 (2H, q); 1.30 (3H, t).

Sources & evidence

ORD record: ord-f41fe768dd6a41ffa84b9bda4ee1c9a8
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008491B2

Reaction notes

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