HCID 19773377, compound → HCID 19773412, compound

HRID 1614271Notes

Reaction equation

HRID 1614271 reaction equation
[ClH:1].[C:2]([N:5]([C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH:11]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:12]2)[CH3:6])(=O)[CH3:3]>O1CCCC1>[ClH:1].[ClH:1].[CH2:2]([N:5]([C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH:11]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:12]2)[CH3:6])[CH3:3]

Participants

3

Reactant 1

HCID 19773377HCID 19773377, compound

Product 1

HCID 19773412HCID 19773412, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Starting from 0.56 g (1.89 mmol) of 5-(N-acetyl-N-methyl-amino)-2-n-propylamino-tetraline-hydrochloride (Example 4.7.8) which is converted into the base, the title compound is obtained as a base by reduction in 20 ml of absolute tetrahydrofuran analogously to Example 4.5.1 c), but using 1.90 ml of 2-molar diboran solution in tetrahydrofuran (THF) as reducing agent. The base is purified by column chromatography (50 g of silica gel, methylene chloride/methanol/conc. ammonia 90:10:0.5) and crystallised as the dihydrochloride analogously to Example 4.1.1, in a yield of 0.33 g (54.6% of theory) and with a melting point of 200° C.

Sources & evidence

ORD record
ord-cc6214b6ad4b446cbc09afdf19b29a49
Source dataset
uspto-grants-1993_03
Patent number
US05196454

Reaction notes

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