4-Piperidinecarboxamide → HCID 22236506, compound

HRID 1743825Notes

Reaction equation

HRID 1743825 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.[CH3:10][O:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14](O)=[O:15].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[CH3:10][O:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1)=[O:15]

Participants

7

Reactant 4

HCID 37724-PiperidinecarboxamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 30175063-Methoxy-2,2-dimethylpropanoic acid

Product 1

HCID 22236506HCID 22236506, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of isonipecotamide (1.0 g, 8.0 mmol), 3-methoxy-2,2-dimethylpropanoic acid (Bulletin of the Chemical Society of Japan 2001, 74, 1695–1702, 1.1 g, 8.0 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU, 3.3 g, 8.8 mmol) and N,N-diisopropylethylamine (1.5 mL, 8.8 mmol) in N,N-dimethylformamide (8 mL) was stirred at room temperature for 18 h. Water (8 mL) was added and the mixture was extracted with ethyl acetate (20 mL×6). Removal of solvent gave a crude of 1-(3-methoxy-2,2-dimethylpropanoyl)piperidine-4-carboxamide as a brown oil, which was dissolved in tetrahydrofuran (15 mL) and added to a suspension of lithium aluminum hydride (2.26 g, 47.7 mmol) in tetrahydrofuran (15 mL) at 0° C. The mixture was stirred at 40° C. for 3 h and quenched with sodium sulfate decahydrate and potassium fluoride. Filtration through a pad of Celite and concentration of the filtrate gave 925 mg (54%) of the title compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 mL×6)
  2. customRemoval of solvent

Sources & evidence

ORD record
ord-3f86b9c06d6447a0963b495ac0c57099
Source dataset
uspto-grants-2006_03
Patent number
US07012080B2

Reaction notes

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