Potassium Cyanide → Benzyl 4-cyano-4-(methylamino)piperidine-1-carboxylate

HRID 1664794Notes

Reaction equation

HRID 1664794 reaction equation
[C-:1]#[N:2].[K+].O=[C:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.Cl.[CH3:22][NH2:23]>O.O.CO.CCOCC>[C:1]([C:5]1([NH:23][CH3:22])[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)#[N:2]

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 6364545Methylamine hydrochloride2×

Product 1

HCID 67440047Benzyl 4-cyano-4-(methylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of potassium cyanide (2.79 g, 42.9 mmol) in water (5 mL) was added to a solution of benzyl 4-oxopiperidine-1-carboxylate (10.0 g, 42.9 mmol) and methylamine hydrochloride (2.90 g, 42.9 mmol) in water/methanol (1:1; 10 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 48 h, additional methylamine hydrochloride (1.45 g, 21.4 mmol) was added. After 18 h, the mixture was diluted with ether, and extracted with ethyl acetate (3×). The combined organic extracts were dried over magnesium sulfate and concentrated down to 50 mL volume. HCl gas was bubbled to this solution for 5 min. The solid precipitated out of the solution was filtered and washed with ether (3×), ethyl acetate (3×) and dried under reduced pressure to give the hydrochloride salt of the title compound. MS 274.1 (M+1).

Workup

  1. waitAfter 18 h
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated down to 50 mL volume
  5. customHCl gas was bubbled to this solution for 5 min
  6. customThe solid precipitated out of the solution
  7. filtrationwas filtered
  8. washwashed with ether (3×), ethyl acetate (3×)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-41754674cd3749fb9cb9f127ffd400a3
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

Loading…