Sodium Bicarbonate → rac-cis-N-((3-Methylpiperidin-2-yl)methyl)quinoline-8-carboxamide

HRID 60792

Reaction equation

HRID 60792 reaction equation
[N+]([O-])([O-])=O.[NH4+].[Ce].COC1C=CC(C[N:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([CH3:20])[C@@H:15]2[CH2:21][NH:22][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[CH:32][CH:31]=[CH:30]3)=[O:24])=CC=1.C([O-])(O)=O.[Na+].C[C@H]1CCCN[C@H]1CNC(C1C=CC=C2C=1N=CC=C2)=O.COC1C=CC(C=O)=CC=1>CC(C)=O.O>[CH3:20][C@H:16]1[CH2:17][CH2:18][CH2:19][NH:14][C@H:15]1[CH2:21][NH:22][C:23]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:34]=1[N:33]=[CH:32][CH:31]=[CH:30]2)=[O:24]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 57418452Ammonium cerium-nitrateHCID 131737121rac-cis-N-((1-(4-methoxybenzyl)-3-methylpiperidin-2-yl)methyl)quinoline-8-carboxamideHCID 131737122rac-cis-N-((3-methylpiperidin-2-yl)methyl)quinoline-8-carboxamide 4-methoxybenzaldehyde

Product 1

HCID 131737120rac-cis-N-((3-Methylpiperidin-2-yl)methyl)quinoline-8-carboxamide

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Cerium ammonium nitrate (1.25 g, 2.28 mmol) was added portionwise to a mixture of rac-cis-N-((1-(4-methoxybenzyl)-3-methylpiperidin-2-yl)methyl)quinoline-8-carboxamide (0.23 g, 0.57 mmol) in acetone/water (10 mL, 9:1 v/v) at 0° C. and allowed to stir at rt for 5 h. Sat. NaHCO3 (aq.) was added and the resulting suspension was stirred at r.t for 10 min, concentrated in vacuo to remove the acetone, then filtered through diatomaceous earth and rinsed with EtOAc. The bi-layer filtrate was extracted with EtOAc and the combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to provide a brown oil as a 1:1 mixture of rac-cis-N-((3-methylpiperidin-2-yl)methyl)quinoline-8-carboxamide/4-methoxybenzaldehyde, which was used as-is without further purification. MS (ESI) 284.13 (M+H).

Workup

  1. stirringthe resulting suspension was stirred at r.t for 10 min
  2. concentrationconcentrated in vacuo
  3. customto remove the acetone
  4. filtrationfiltered through diatomaceous earth
  5. washrinsed with EtOAc
  6. extractionThe bi-layer filtrate was extracted with EtOAc
  7. washthe combined organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto provide a brown oil
  11. customwithout further purification

Sources & evidence

ORD record
ord-3f372c9674ec4a14ba051a8feaf2fcad
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Linked notes

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