Hydrochloric Acid → 3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethylamino]-propoxy}-phenylamine

HRID 902632Notes

Reaction equation

HRID 902632 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[C:35]=2[Cl:44])[CH2:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=1)(C)(C)C.Cl>O1CCOCC1>[Cl:44][C:35]1[C:36]([C:40]([F:41])([F:42])[F:43])=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][N:18]([CH2:19][CH:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:17][CH2:16][CH2:15][O:14][C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10175511(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 101287483-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethylamino]-propoxy}-phenylamineYield 96.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To N-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-carbamic acid tert-butyl ester (492 mg, 0.77 mmol) dissolved in dioxane (5 mL) was added a 4.0 M solution of HCl in dioxane (5 mL). The solution was maintained for 20 hours after which the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane and washed twice with saturated NaHCO3, dried over Na2SO4, and concentrated to give 0.4 g (0.74 mmol, 96%) of the title compound as a yellow oil. MS (ESI) 539.2

Workup

  1. temperatureThe solution was maintained for 20 hours after which the solvent
  2. customwas removed under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed twice with saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-517b823aa52946ef8ca86369b66d95bb
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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