Hydrochloric Acid → HCID 69253147, compound

HRID 902701Notes

Reaction equation

HRID 902701 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[C:41]=3[Cl:50])[CH2:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO>[ClH:50].[Cl:50][C:41]1[C:42]([C:46]([F:48])([F:47])[F:49])=[CH:43][CH:44]=[CH:45][C:40]=1[CH2:39][N:24]([CH2:25][CH:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:23][CH2:22][CH2:21][O:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69252373HCID 69252373, compound

Product 1

HCID 69253147HCID 69253147, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (475 mg, 0.67 mmol) in a 1:1 mixture of 3M HCl (aq.) and methanol (30 mL total) was stirred at room temperature for 18 hours. The mixture was concentrated in vacuo, and the crude material was dissolved in EtOAc. The EtOAc solution was washed with saturated aqueous sodium bicarbonate solution (3×) and brine (1×), dried over sodium sulfate, and filtered. The EtOAc extracts were concentrated and the crude piperazine was treated with 1 M HCl (Et2O) to afford the title compound as a solid, 415 mg (100%). MS(ES) m/e 608.4 (M+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe crude material was dissolved in EtOAc
  3. washThe EtOAc solution was washed with saturated aqueous sodium bicarbonate solution (3×) and brine (1×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe EtOAc extracts were concentrated
  7. additionthe crude piperazine was treated with 1 M HCl (Et2O)

Sources & evidence

ORD record
ord-3d602e8c7c4f475982d52a4b380b2533
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

Loading…