1,2-Dichloroethane → HCID 89677152, compound

HRID 2278231Notes

Reaction equation

HRID 2278231 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[C:9]([O:15][C:16]([F:19])([F:18])[F:17])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N:20]1([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.ClCCCl.[Na]>O>[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][N:23]3[CH2:22][CH2:21][N:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24]3)=[C:9]([O:15][C:16]([F:19])([F:18])[F:17])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5360545SodiumHCID 89676876HCID 89676876, compound

Product 1

HCID 89677152HCID 89677152, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 40 mL vial was charged with 4-(morpholin-4-yl)-2-(trifluoromethoxy)benzaldehyde (400 mg, 1.45 mmol, 1.00 equiv), tert-butyl piperazine-1-carboxylate (270 mg, 1.45 mmol, 1.00 equiv), 1,2-dichloroethane (15 mL). The resulting solution was stirred for 1 h at room temperature. Sodium triacetoxyhydroborate (925 mg, 4.36 mmol, 3.00 equiv) was added. The resulting solution was stirred for 15 hours at room temperature. The reaction progress was monitored by LCMS. The resulting solution was diluted with 15 mL of water. The resulting solution was extracted with dichloromethane (3×15 mL) and the organic layers combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/3) to provide 590 mg (91% yield) of tert-butyl 4-[[4-(morpholin-4-yl)-2-(trifluoromethoxy)phenyl]methyl]piperazine-1-carboxylate as yellow oil. LCMS (ESI, m/z): 446 [M+H]+.

Workup

  1. stirringThe resulting solution was stirred for 15 hours at room temperature
  2. extractionThe resulting solution was extracted with dichloromethane (3×15 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/3)

Sources & evidence

ORD record
ord-ec8b39e3bef7485584b315205ac404ff
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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