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

HRID 1821602Notes

Reaction equation

HRID 1821602 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-2ab7dbd4e7c34e89a6639c144c9f2b8b
Source dataset
uspto-grants-2009_10
Patent number
US07608592B2

Reaction notes

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