(1-methyl-1H-imidazol-2-yl)methanamine → ({2-[4-(dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinyl}methyl)[(1-methyl-1H-imidazol-2-yl)methyl]amine

HRID 68640Notes

Reaction equation

HRID 68640 reaction equation
[CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:19]=O)[CH:15]=2)[CH2:10]1)[CH2:2][CH3:3].C[Si](C)(C)CCOCN1C=CN=C1C=O.[CH3:39][N:40]1[CH:44]=[CH:43][N:42]=[C:41]1[CH2:45][NH2:46]>>[CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][NH:46][CH2:45][C:41]3[N:40]([CH3:39])[CH:44]=[CH:43][N:42]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 533842(1-methyl-1H-imidazol-2-yl)methanamineHCID 136002351-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehydeHCID 86654292HCID 86654292, compound

Product 1

HCID 67163530({2-[4-(dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinyl}methyl)[(1-methyl-1H-imidazol-2-yl)methyl]amine

Procedure

The same procedure as a series of reactions of Example 1 was carried out, except that the compound 22 was used in place of 1-({[2-(trimethylsilyl)ethyloxy]methyl}-1H-imidazole-2-carboaldehyde and [(1-methyl-1H-imidazol-2-yl)methyl]amine was used in place of {[4-(methyloxy)phenyl]methyl}amine to obtain ({2-[4-(dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinyl}methyl)[(1-methyl-1H-imidazol-2-yl)methyl]amine (compound 23-a). The same procedure as a series of reactions of Example 17 was carried out, except that the obtained compound 23-a was used in place of the compound 16, to obtain the title compound having the following physical properties.

Sources & evidence

ORD record
ord-6150af45124e4459b862d08890559d94
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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