Hydrochloric Acid → HCID 11753486, compound

HRID 1678154Notes

Reaction equation

HRID 1678154 reaction equation
[CH2:1]([O:3][P:4](=[O:38])([O:35][CH2:36][CH3:37])[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=3)[C:16]3[C:21]([C:22]=2[CH:23]=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)[CH3:2].[ClH:39]>CO>[ClH:39].[CH2:1]([O:3][P:4](=[O:38])([O:35][CH2:36][CH3:37])[O:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:15]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([CH3:32])([CH3:33])[CH3:34])=[CH:29][CH:30]=3)[C:16]3[C:21]([C:22]=2[CH:23]=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:13]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11753487HCID 11753487, compound

Product 1

HCID 11753486HCID 11753486, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phosphoric acid 2-{4-[1-(4-tert-butylphenyl)-3-formyl-1H-indol-2-yl]-piperazin-1-yl}-ethyl ester diethyl ester (90 mg, 0.166 mmol) is dissolved in methanol and treated with 1M ethereal hydrochloric acid. The solvents are reduced to half and triturated with ether to obtain phosphoric acid 2-{4-[1-(4-tert-butylphenyl)-3-formyl-1H-indol-2-yl]-piperazin-1-yl}-ethyl ester diethyl ester hydrochloride (85 mg, 89% yield) as a solid. ESI/MS 542 (M+H), RT=3.52 min; 1H NMR 10.06 (1H, s); 8.11 (1H, d, J=6 Hz); 7.69 (2H, d, J=9 Hz); 7.51 (2H, d, J=6 Hz); 7.24 (2H, m); 6.96 (1H, d, J=6 Hz); 4.33 (2H, br s); 4.10 (4H, q); 3.68 (2H, br s); 3.39 (6H, br s); 3.03 (2H, br s); 1.37 (9H, s); 1.27 (6H, t); 13C NMR 229.09; 209.60; 197.36; 184.62; 183.17; 154.06; 151.49; 135.32; 133.45; 127.20; 126.81; 124.98; 122.94; 119.71; 113.77; 109.99; 109.53; 106.00; 63.72; 63.65; 51.36; 48.00; 34.59; 31.06; 15.97; 15.88.

Workup

  1. customtriturated with ether

Sources & evidence

ORD record
ord-4ce6392bb6b94fcf82b38d2eb44de4a1
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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