1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehyde → Methyl 2-[4-(dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinecarboxylate

HRID 68637Notes

Reaction equation

HRID 68637 reaction equation
[CH2:1]([N:4]([CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH:8]=O)[CH2:2][CH3:3].C[Si](C)(C)CCOCN1C=CN=C1C=O.Cl.[CH2:29]1[C:38]2[C:33](=[CH:34][C:35]([C:39]([O:41][CH3:42])=[O:40])=[CH:36][CH:37]=2)[CH2:32][CH2:31][NH:30]1>>[CH2:1]([N:4]([CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][N:30]1[CH2:31][CH2:32][C:33]2[C:38](=[CH:37][CH:36]=[C:35]([C:39]([O:41][CH3:42])=[O:40])[CH:34]=2)[CH2:29]1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 136002351-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehydeHCID 226111444-(Dipropylamino)butanalHCID 42614607Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride

Product 1

HCID 67164447Methyl 2-[4-(dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinecarboxylate

Procedure

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

Sources & evidence

ORD record
ord-f16b09ab72e44430aa31ef3ad1e9af98
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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