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Acetic Acid → (2-(1-(2-Cyano-4-trifluoromethylphenyl)piperidin-4-ylamino)-ethyl)carbamic acid tert-butyl ester

HRID 842781
Notes
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Reaction equation

HRID 842781 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)#[N:2].[NH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(O)(=O)C.ClC(Cl)C.C([BH3-])#N.[Na+]>CO>[C:26]([O:25][C:24](=[O:30])[NH:23][CH2:22][CH2:21][NH:20][CH:16]1[CH2:17][CH2:18][N:13]([C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]=2[C:1]#[N:2])[CH2:14][CH2:15]1)([CH3:29])([CH3:27])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 22615393N-(2-Cyano-4-trifluoromethylphenyl)-4-piperidone

Product 1

HCID 18727097
(2-(1-(2-Cyano-4-trifluoromethylphenyl)piperidin-4-ylamino)-ethyl)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 25 (535 mg, 1.99 mmol), 1 (335 mg, 2.09 mmol), and acetic acid (629 mg, 10.48 mmol) in methanol(2 mL)/dichloroethane(1 mL) was treated with sodium cyanoborohydride (130 mg, 2.06 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium carbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 4 mm, 10% EtOH-90% CHCl3) afforded the title compound (26).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d87d1e5e969244feadcc07b3064c15af
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06376503B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes