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Triethylamine → 1-[3,5-Bis(trifluoromethyl)benzoyl]-4-(benzyloxycarbonyl)-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazine

HRID 1374974
Notes
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Reaction equation

HRID 1374974 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][C:31]=1[CH3:32])[CH2:22][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1.C(N(CC)CC)C.[F:40][C:41]([F:56])([F:55])[C:42]1[CH:43]=[C:44]([CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1)[C:45](Cl)=[O:46]>ClCCl>[F:40][C:41]([F:55])([F:56])[C:42]1[CH:43]=[C:44]([CH:48]=[C:49]([C:51]([F:54])([F:52])[F:53])[CH:50]=1)[C:45]([N:24]1[CH2:25][CH2:26][N:27]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:28][CH:23]1[CH2:22][C:21]1[CH:29]=[CH:30][C:31]([CH3:32])=[C:19]([O:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH3:12])[CH:20]=1)=[O:46]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 179640282-[3-[(2-Methoxyethoxy)methoxy]-4-methylbenzyl]piperazine

Product 1

HCID 179642461-[3,5-Bis(trifluoromethyl)benzoyl]-4-(benzyloxycarbonyl)-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of benzyloxycarbonyl chloride (0.75 g) in dichloromethane (1 ml) was added dropwise over 5 minutes to an ice-cooled solution of 2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazine (1.27 g) obtained by above procedure and triethylamine (2.2 ml) in dichloromethane (10 ml) below 5° C. After the mixture was stirred for 30 minutes at the same temperature, a solution of 3,5-bis(trifluoromethyl)-benzoyl chloride (0.93 ml) in dichloromethane (1.0 ml) was added dropwise to the mixture over 10 minutes below 5° C. After being stirred for 30 minutes at the same temperature, the reaction mixture was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using mixed solvents of toluene and ethyl acetate (5:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give 1-[3,5-bis(trifluoromethyl)benzoyl]-4-(benzyloxycarbonyl)-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazine (1.61 g) as an oil.

Workup

  1. stirringAfter being stirred for 30 minutes at the same temperature
  2. washthe reaction mixture was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additionmixed solvents of toluene and ethyl acetate (5:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6dc9d51ce4b544dcb9f552d108498e4c
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07166598B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes