N-Benzylbut-3-en-1-amine → HCID 53673348, compound

HRID 2179407Notes

Reaction equation

HRID 2179407 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:13].[C:14]([OH:18])(=[O:17])[CH:15]=O>C(#N)C.O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([OH:13])[CH2:12][CH:15]1[C:14]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4366091N-Benzylbut-3-en-1-amineHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 53673348HCID 53673348, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The product of step A (24.5 g, 0.15 mol) was dissolved in acetonitrile/water (1:1, 500 mL) and treated with glyoxylic acid monohydrate (15.3 g, 0.17 mol). The resulting solution was allowed to stir at ambient temperature for 12 h. The reaction mixture was concentrated in vacuo, made basic via addition of 1 M NaOH (500 mL) and extracted with dichloromethane (3×200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to afford crude 1-benzyl-4-hydroxypiperidine-2-carboxylic acid (24 g, 69%) as a colorless oil which was used without further purification: 1H NMR (CDCl3, 400 MHz) δ 7.38-7.27 (m, 5H), 4.82 (t, J=5.2 Hz, 1H), 3.73-3.59 (m, 2H), 3.30 (d, J=4.8 Hz, 1H), 3.03 (dd, J=12.0, 6.4 Hz, 1H), 2.50-2.43 (m, 1H), 2.29-2.19 (m 1H), 2.08-1.98 (m, 1H), 1.97-1.88 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionmade basic via addition of 1 M NaOH (500 mL)
  3. extractionextracted with dichloromethane (3×200 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eeeb76c266264c4ca5d15e373b72bfad
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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