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Dichloromethane → 4-[3-Piperazin-1-yl-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]morpholine

HRID 2218850
Notes
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Reaction equation

HRID 2218850 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[CH:26]2[CH2:31][C:30]([CH3:33])([CH3:32])[CH2:29][C:28]([CH3:35])([CH3:34])[CH2:27]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[N:11]1([C:14]2[CH:19]=[C:18]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[CH:17]=[CH:16][C:15]=2[CH:26]2[CH2:27][C:28]([CH3:35])([CH3:34])[CH2:29][C:30]([CH3:32])([CH3:33])[CH2:31]2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 597693874-[5-Morpholin-4-yl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 231426114-[3-Piperazin-1-yl-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]morpholineYield 51.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 4-[5-morpholin-4-yl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester (103 mg, 0.212 mmol) produced in Example (81d), trifluoroacetic acid (1 mL, 13.0 mmol) and dichloromethane (2 mL) was stirred for 1 hour at room temperature. Ethyl acetate and saturated aqueous solution of sodium hydrogencarbonate were added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was washed with water and brine in that order and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 42 mg of the title compound as a colorless oil.

Workup

  1. washThe separated organic layer was washed with water and brine in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-430813c6acd94847a6d8130cce11def0
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07410971B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes