Acetic Acid → HCID 86669224, compound

HRID 2366842Notes

Reaction equation

HRID 2366842 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[CH:7]([NH:22][CH:23]=[O:24])[CH2:6][CH:5]1[CH3:25])(=[O:3])[CH3:2].[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(O)(=O)C.C([O-])(O)=O.[Na+]>ClC(Cl)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:22][CH:23]=[O:24])[CH2:6][C@@H:5]1[CH3:25])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 86669231HCID 86669231, compound

Product 1

HCID 86669224HCID 86669224, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of [1-acetyl-6-(4-formylphenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide (for a preparation see Intermediate 48) (95 g, 0.25 mol) and piperidine (31 g, 0.3 mol) in solution in dichloroethane (2 L) were added at room temperature triacetoxysodiumborohydride (70 g, 0.33 mol) and acetic acid (33 g). After stirring 2 hours a t.l.c monitoring indicated the completion of the reaction and the mixture was poured into a saturated solution of NaHCO3. The organic phase was extracted after addition of DCM (500 mL) and washed with brine (100 mL), dried over Na2SO4, filtered and evaporated to dryness. Trituration of the residue in a mixture of DCM/hexane afforded the title compound (109 g, 95.6%) as an off white solid. LC/MS (Method E) m/z 406 [M+H]+, Rt=2.22 min;

Workup

  1. customthe completion of the reaction
  2. extractionThe organic phase was extracted
  3. additionafter addition of DCM (500 mL)
  4. washwashed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. additionTrituration of the residue in a mixture of DCM/hexane

Sources & evidence

ORD record
ord-bacf66d04d464fc3bcdef4f59b2a61ac
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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