Hydrochloric Acid → 2,2-Dimethyl-1-(2-hydroxyethyl)-7-methoxy-3-methylamino-1,2,3,4-tetrahydronaphthalene hydrochloride

HRID 2287051Notes

Reaction equation

HRID 2287051 reaction equation
[CH3:1][C:2]1([CH3:29])[CH:11]([N:12]([CH3:23])S(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:24][CH3:25])=[CH:7][CH:8]=2)[C:3]1=[CH:26][CH2:27][OH:28].[Na].[ClH:31]>N>[ClH:31].[CH3:1][C:2]1([CH3:29])[CH:11]([NH:12][CH3:23])[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:24][CH3:25])=[CH:7][CH:8]=2)[CH:3]1[CH2:26][CH2:27][OH:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 54324160HCID 54324160, compound

Product 1

HCID 234608602,2-Dimethyl-1-(2-hydroxyethyl)-7-methoxy-3-methylamino-1,2,3,4-tetrahydronaphthalene hydrochloride

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

This compound, described already in Examples 12 and 13, can also be prepared as described in Example 13, however, starting from 2,2-dimethyl-1-(2-hydroxyethylidene)-7-methoxy-3-(N-methyl-p-toluenesulfonamido)-1,2,3,4-tetrahydronaphthalene. In this case, both the reduction of the olefinic double bond and the reductive cleavage of the p-toluenesulphonamido group are effectuated by the sodium metal dissolving in liquid ammonia. The endpoint of the reduction is reached if the blue colour persists for some 15 minutes. In this case again, a mixture of two stereoisomers is obtained, the total yield being 87% of crystalline hydrochloride.

Workup

  1. customcan also be prepared
  2. additionIn this case again, a mixture of two stereoisomers
  3. customis obtained
  4. customthe total yield

Sources & evidence

ORD record
ord-91291e0e3e7d481aabb8db8b1fd3d2c6
Source dataset
uspto-grants-1981_05
Patent number
US04268673

Reaction notes

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