Hydrochloric Acid → HCID 21071634, compound

HRID 1371923Notes

Reaction equation

HRID 1371923 reaction equation
Cl.C([O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]([F:34])([F:33])[F:32])[CH:24]=1)C1C=CC=CC=1.Cl>[Pd].CCO>[OH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]([F:34])([F:32])[F:33])[CH:24]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21071626HCID 21071626, compound

Product 1

HCID 21071634HCID 21071634, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine N-(2-(5-benzyloxy-1H-indol-3-yl)ethyl)-3-(2,2,2-trifluoroethoxy)benzylamine hydrochloride (295 mg, 0.6 mmol) and 25 mL EtOH and treat with 0.3 mL 5 N HCl and 300 mg 5% Pd/C and hydrogenate at atmospheric pressure overnight. Filter the reaction through a pad of celite and concentrate to dryness then chromatograph on silica gel to give the title compound: ISMS 365 (M+1); 1H NMR (DMSO-d6) 10.6 (bs, 1H), 9.4 (bs, 2H), 8.75 (s, 1H), 7.45–6.6 (m, 7H), 4.9–4.7 (m, 2H), 4.2 (bs, 2H), 3.2–2.9 (m, 4H).

Workup

  1. filtrationFilter
  2. customthe reaction through a pad of celite
  3. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-b3f739757a5544be802ba22cf8fc0b38
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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