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Sodium Carbonate → HCID 21713907, compound

HRID 649808
Notes
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Reaction equation

HRID 649808 reaction equation
[CH:1]([CH2:3][N:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])=O.[F:19][C:20]([F:35])([F:34])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>O.ClCCCl.C(O)(=O)C>[CH:7]1([C:5]([N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:3][CH2:1][N:31]2[CH2:30][CH2:29][N:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][C:20]([F:34])([F:19])[F:35])[CH2:33][CH2:32]2)=[O:6])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 107529251-(2-Trifluoromethoxyphenyl)piperazineHCID 21713921N-Formylmethyl-N-(2-pyridyl)cyclohexanecarboxamide

Product 1

HCID 21713907HCID 21713907, compoundYield 51.1%

Reagents, catalysts & solvents 3

HCID 11
1,2-Dichloroethane
Solvent
HCID 176Acetic AcidSolvent
HCID 962WaterSolvent

Procedure

A mixture comprising 0.459 g of Compound 1B, 0.445 g of 1-(2-trifluoromethoxyphenyl)piperaine (prepared as described by D. Clarke et al, in European Patent EP 711 757, 1996), 0.634 g sodium triacetoxyborohydride, 0.23 mL of glacial acetic acid and 15 mL of 1,2-dichloroethane was stirred for 4 h, under a nitrogen atmosphere. The resultant solution was then kept overnight at room temperature, followed by the addition of 10 mL of water, and alkalinization with a 20% aqueous Na2CO3 solution. This was followed by separation of phases, with the isolated aqueous phase being extracted with 2×20 mL dichloromethane, and with the collected organic phases being dried over anhydrous sodium sulphate. This was followed by the removal of solvents, via vacuum evaporation to dryness. The obtained product residue was purified by flash chromatography (ethyl acetate—petroleum ether gradient 90:10 to 10:0). This was followed by evaporation of the solvents, affording 0.44 g of the title compound (yield 51%).

Workup

  1. customThis was followed by separation of phases, with the isolated aqueous phase
  2. extractionbeing extracted with 2×20 mL dichloromethane
  3. dry with materialwith the collected organic phases being dried over anhydrous sodium sulphate
  4. customThis was followed by the removal of solvents, via vacuum evaporation to dryness
  5. customThe obtained product residue was purified by flash chromatography (ethyl acetate—petroleum ether gradient 90:10 to 10:0)
  6. customThis was followed by evaporation of the solvents

Sources & evidence

ORD record
ord-0a90b7411b3c4eba8be42f1ec1927717
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06271234B1

Reaction notes

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