Hydrochloric Acid → Bicyclo[3.1.1]heptane-3-methanamine, 2,6,6-trimethyl-, hydrochloride (1:1)

HRID 1679609Notes

Reaction equation

HRID 1679609 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH:7]2[CH2:9][CH:5]([C:6]2([CH3:11])[CH3:10])[CH:4]1[CH3:12].[ClH:13]>CCCCC>[ClH:13].[NH2:1][CH2:2][CH:3]1[CH2:8][CH:7]2[CH2:9][CH:5]([C:6]2([CH3:11])[CH3:10])[CH:4]1[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 106576Bicyclo(3.1.1)heptane-3-methanamine, 2,6,6-trimethyl-

Product 1

HCID 106575Bicyclo[3.1.1]heptane-3-methanamine, 2,6,6-trimethyl-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

300 g of ethanol and 50 g of Raney cobalt are introduced into a high pressure vessel of 2.5 liters capacity and the air is flushed out with nitrogen. The reaction mixture is then heated to 80° C and placed under a hydrogen pressure of 150 atmospheres. 200 g of (+)-3-formylpinane are introduced in the course of 6 hours and after a further 2 hours the reaction mixture is cooled and the pressure is released. 650 g of a mixture are obtained; its fractional distillation gives 106 g of (+)-3-aminomethylpinane boiling at from 110° to 111° C/20 mm Hg. 120 g of the 3-aminomethylpinane are dissolved in 1.3 l of pentane and dry hydrogen chloride is passed into the solution at from 0° to 5° C, whilst stirring. When free amine is no longer detectable the crystals produced are filtered off and dried. 142 g of (+)-3-aminomethylpinane hydrochloride of optical rotation [α]D23 = + 35.4° (c = 1, methanol) are obtained.

Workup

  1. customis passed into the solution at from 0° to 5° C
  2. customproduced
  3. filtrationare filtered off
  4. customdried

Sources & evidence

ORD record
ord-17abaa3a08a84b509215bcafd9aa6be0
Source dataset
uspto-grants-1978_03
Patent number
US04081477

Reaction notes

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