2,2,6,6-Tetramethylpiperidine → HCID 178418821, compound

HRID 1895867Notes

Reaction equation

HRID 1895867 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[NH:3]1.[Li:11]CCCC.C1(N=CC2C=CC(OC)=CC=2C)CCCCC1.CN(OC)C(C1CC1)=O.[NH4+].[Cl-]>C1COCC1>[Li:11][N:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]1([CH3:10])[CH3:1]

Participants

7

Reactant 5

HCID 130352,2,6,6-TetramethylpiperidineHCID 25517Ammonium ChlorideHCID 15643267N-Methoxy-N-methylcyclopropanecarboxamideHCID 57893115(E)-N-Cyclohexyl-1-(4-methoxy-2-methylphenyl)methanimineHCID 178418339Butyllithium

Product 1

HCID 178418821HCID 178418821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Lithium tetramethylpiperidide was prepared by the treatment of 2,2,6,6-tetramethylpiperidine (1.0 g; 7.0 mmol) in THF (17 mL) with n-BuLi (1.6 M in hexanes; 8.0 mmol) dropwise at −15° C. After 15 min at −15° C., a solution of cyclohexyl(4-methoxy-2-methylbenzylidene)amine (660 mg; 2.86 mmol) in THF (3 mL) was added dropwise to give a purple solution. The reaction mixture was allowed to warm to 0° C. over a 20-min period then a solution of N-methyl-N-methoxycyclopropanecarboxamide (630 mg: 4.4 mmol) in THF (2 mL) was added in one portion while at 0° C. The reaction mixture was kept at room temperature for 30 min and then added to saturated aq. NH4Cl. The solution was extracted with diethyl ether and the organic phase was washed with saturated aq. NaCl, dried and concentrated in vacuo.

Workup

  1. customto give a purple solution
  2. waitThe reaction mixture was kept at room temperature for 30 min
  3. extractionThe solution was extracted with diethyl ether
  4. washthe organic phase was washed with saturated aq. NaCl
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98d2ddfd175f4c13a424e93d674b30ab
Source dataset
uspto-grants-2013_08
Patent number
US08518874B2

Reaction notes

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