2-Chloro-N,N-dimethylethylamine → Camphor

HRID 1168462Notes

Reaction equation

HRID 1168462 reaction equation
[NH2-].[Na+].C1([C@@:9]2([OH:19])[CH2:14][C@@H:13]3[C:15]([CH3:17])([CH3:16])[C@@:10]2([CH3:18])[CH2:11][CH2:12]3)C=CC=CC=1.ClCCN(C)C>O1CCOCC1>[C:10]12([CH3:18])[C:15]([CH3:17])([CH3:16])[CH:13]([CH2:12][CH2:11]1)[CH2:14][C:9]2=[O:19]

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24533Sodium amideHCID 10721413Phenylborneol

Product 1

HCID 2537Camphor

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of 45.5 g (1.05 mole) sodium amide (content: 90% by weight/weight) and 500 ml of anhydrous dioxane a mixture of 220 g of the colourless oil obtained by the hydrolysis containing (1R,2S,4R)-(−)-2-[phenyl]-1,7,7-tri-[methyl]-bicyclo[2.2.1]heptane-2-ol, and 100 ml of anhydrous dioxane is added at the boiling point within half an hour. The mixture is heated to boiling for 2 hours, whereupon 113.0 g (1.05 mole) of (2-{chloro}-ethyl)-dimethylamine are added and the reaction mixture is heated to boiling for a further period of 4 hours.

Workup

  1. customobtained by the hydrolysis
  2. additionis added at the boiling point within half an hour
  3. temperatureThe mixture is heated
  4. additionare added
  5. temperaturethe reaction mixture is heated

Sources & evidence

ORD record
ord-3939d9681d2e47729ff100525c01a0fc
Source dataset
uspto-grants-2003_09
Patent number
US06624201B2

Reaction notes

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