Morpholine → 4-(Pyridin-3-yl)-piperidine-4-carboxylic acid morpholine-amide

HRID 400079Notes

Reaction equation

HRID 400079 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:2]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.Cl.C([N:25]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[N:16]1([C:13]([NH2:25])=[O:15])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[CH:2]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 542592754-(Pyridin-3-yl)piperidine-4-carboxylic acid

Product 1

HCID 1317209034-(Pyridin-3-yl)-piperidine-4-carboxylic acid morpholine-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Combine 1-benzyl-(4-(pyridin-3-yl)-piperidine-4-carboxylic acid (2.5 g, 8.4 mmol) and morpholine (1.5 g, 16.9 mmol) in dimethylformamide (65 mL). Add 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (2.2 g), 1-hydroxy-benzotriazole hydrate (HOBt) (1.6 g), and dimethylformamide (25 mL). After 24 hours, pour the reaction mixture into a saturated aqueous sodium bicarbonate solution and extract twice with diethyl ether. Combine the organic layers, dry over MgSO4, filter, and concentrate to about 50 mL to give solid. Collect the solid by filtration, rinse with diethyl ether, and dry to give 1-benzyl-(4-(pyridin-3-yl)-piperidine-4-carboxylic acid morpholine-amide: Rf =0.67 (silica gel, dichloromethane/methanol/concentrated ammonia 90/10/0.5).

Workup

  1. extractionextract twice with diethyl ether
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate to about 50 mL
  5. customto give solid
  6. customCollect the solid
  7. filtrationby filtration
  8. washrinse with diethyl ether
  9. customdry

Sources & evidence

ORD record
ord-6677ae4a50b74069b7acef3c75381988
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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