Ammonia → (+/-)-2-Benzyl-2-(3'-dimethylaminopropoxy)-1,7,7-trimethyl-bicyclo(2,2,1) heptane

HRID 66560

Reaction equation

HRID 66560 reaction equation
[NH2-].[Na+].[CH2:3]([C:10]1([OH:20])[CH2:15][CH:14]2[C:16]([CH3:18])([CH3:17])[C:11]1([CH3:19])[CH2:12][CH2:13]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N.[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26]Cl.C(O)(=O)C(C(C(O)=O)O)O.Cl.[OH-].[NH4+]>C1C=CC=CC=1.O>[CH2:3]([C:10]1([O:20][CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:22])[CH2:15][CH:14]2[C:16]([CH3:17])([CH3:18])[C:11]1([CH3:19])[CH2:12][CH2:13]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

10

Reactant 7

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8752,3-Dihydroxybutanedioic AcidHCID 14923Ammonium HydroxideHCID 24533Sodium amideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 2511722-Benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Product 1

HCID 13749826(+/-)-2-Benzyl-2-(3'-dimethylaminopropoxy)-1,7,7-trimethyl-bicyclo(2,2,1) heptane

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A suspension of 3.9 g (0.1 mole) of sodium amide in 100 ml of anhydrous benzene is heated to boiling, and a solution of 24.4 g (0.1 mole) of (±)-2-benzyl-1,7,7-trimethyl-bicyclo(2,2,1)-heptan-2-ol in 100 ml of anhydrous benzene is added dropwise, under continuous stirring. When the addition of the above solution is completed the reaction mixture is boiled until the formation of ammonia gas is ceased, and while further continuing the stirring, a solution of 13.4 g (0.11 mole) of 1-dimethylamino-3-chloro-propane in 20 ml of anhydrous benzene is added. After boiling the mixture for further 6 hours it is cooled to 30° C., washed three times with 40 ml of water each, and extracted with a solution of 15 g (0.1 mole) of tartaric acid in 50 ml of water or with 0.11 mole of diluted aqueous hydrochloric acid. The aqueous solution cooled to 0°-5° C. is made alkaline to pH 10 with concentrated ammonium hydroxide. The base separated as an oil is extracted with dichloroethane. On distilling off the solvent, the residue is fractionated in vacuo.

Workup

  1. temperatureis heated
  2. additionWhen the addition of the above solution
  3. customfor further 6 hours
  4. washwashed three times with 40 ml of water each, and
  5. temperatureThe aqueous solution cooled to 0°-5° C.
  6. customThe base separated as an oil
  7. extractionis extracted with dichloroethane
  8. distillationOn distilling off the solvent

Sources & evidence

ORD record
ord-138ae41e29694560a93721ec503396c0
Source dataset
uspto-grants-1982_08
Patent number
US04342762

Linked notes

Loading…