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Acetic Acid → 4-(N (t-butoxycarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(3-(6-((4-methoxybenzyl)oxy)-3-cyanophenyl)prop-2-en-1-yl)benzenamine

HRID 1700297
Notes
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Reaction equation

HRID 1700297 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[C:22]([F:25])([F:24])[F:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]([C:28]1[CH:29]=[C:30]([CH:44]=[CH:45][CH:46]=O)[C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[CH:32][CH:33]=1)#[N:27].C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:46][CH:45]=[CH:44][C:30]3[C:31]([O:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=4)=[CH:32][CH:33]=[C:28]([C:26]#[N:27])[CH:29]=3)=[CH:17][C:16]=2[C:22]([F:25])([F:23])[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 22180984Tert-butyl 4-(4-amino-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylateHCID 734371553-Cyano-6-((4-methoxybenzyl)oxy)-1-(2-formylethenyl)benzene

Product 1

HCID 701667714-(N (t-butoxycarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(3-(6-((4-methoxybenzyl)oxy)-3-cyanophenyl)prop-2-en-1-yl)benzenamine
Yield 65.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-[(N-(t-butoxycarbonyl)piperidin-4-yl)oxy]-3-trifluoromethylbenzenamine (4.9 g) and 3-cyano-6-((4-methoxybenzyl)oxy)-1-(2-formylethenyl)benzene (4 g) in MeOH (80 mL) was added acetic acid (0.73 g). The resulting solution was stirred at ambient temperature for 15 minutes and then NaCNBH3 was added. The resulting solution was stirred at ambient temperature for 1 hour and concentrated. The residue was taken up in 100 mL of aqueous NaHCO3 and extracted with ethyl acetate (3×). The organic layer was dried, concentrated and purified on silica gel column (ethyl acetate/hexane, 3:7) to afford 5.7 g of 4-(N (t-butoxycarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(3-(6-((4-methoxybenzyl)oxy)-3-cyanophenyl)prop-2-en-1-yl)benzenamine as a yellow oil.

Workup

  1. stirringThe resulting solution was stirred at ambient temperature for 1 hour
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (3×)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. custompurified on silica gel column (ethyl acetate/hexane, 3:7)

Sources & evidence

ORD record
ord-77e4456f52cf40e5acd91df8e8757269
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06350761B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes