Ammonium Chloride → HCID 14230309, compound

HRID 35241Notes

Reaction equation

HRID 35241 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]2[CH3:28])=O)=[CH:7][CH:6]=1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-:35].[NH4+]>O1CCCC1>[ClH:35].[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]2[CH3:28])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 21295810N-(4-acetoxyphenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

Product 1

HCID 14230309HCID 14230309, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-(4-acetoxyphenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (33.0 g, 0.086 m) in 50 ml of tetrahydrofuran was added dropwise to a stirred suspension of lithium aluminum hydride (8.8 g, 0.233 m) in 500 ml dry tetrahydrofuran maintained under nitrogen. The mixture was stirred at ambient temperature for 24 hours, then cooled with an ice bath and carefully treated with 24 ml of a saturated ammonium chloride solution. The salts were removed by filtration, the filtrate dried over MgSO4 and evaporated on an aspirator to a pale yellow oil, 23.2 g (77% yield). The hydrochloride salt was prepared in 100 ml of 1:1 isopropanol:methanol and recrystallization and vacuum drying of the white solid gave 14.7 g of N-(4-hydroxyphenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride, m.p. 225°-226°.

Workup

  1. temperaturemaintained under nitrogen
  2. temperaturecooled with an ice bath
  3. customThe salts were removed by filtration
  4. dry with materialthe filtrate dried over MgSO4
  5. customevaporated on an aspirator to a pale yellow oil, 23.2 g (77% yield)
  6. custommethanol and recrystallization and vacuum
  7. customdrying of the white solid

Sources & evidence

ORD record
ord-396c8990cc024b6a8c8fcc977e0f6b2a
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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