Hydrochloric Acid → HCID 11753486, compound

HRID 751371Notes

Reaction equation

HRID 751371 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-9dd16b44cdc64828a4f2af932e9b1542
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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