Reaction equation
C1C2C(=CC=CC=2)C=C[NH2+]1.[Cl-].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:22]([CH:43]([CH3:45])[CH3:44])([C:41]#[N:42])[CH2:23][CH2:24][CH2:25][C:26]2[CH2:35][C:34]3[C:29](=[CH:30][C:31]([O:38][CH3:39])=[C:32]([O:36][CH3:37])[CH:33]=3)[CH2:28][N+:27]=2[CH3:40])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]>>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:22]([CH:43]([CH3:45])[CH3:44])([C:41]#[N:42])[CH2:23][CH2:24][CH2:25][CH:26]2[CH2:35][C:34]3[C:29](=[CH:30][C:31]([O:38][CH3:39])=[C:32]([O:36][CH3:37])[CH:33]=3)[CH2:28][N:27]2[CH3:40])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]Participants
Procedure
The dihydroisoquinolinium salt of formula 34 is then hydrogenated to produce a compound of formula 1 (step 6). This reaction is performed using a suitable hydrogenating agent, preferably a boron hydride derivative, particularly NaBH4. The solvent used is preferably a lower alkanol, particularly MeOH. The reaction is carried out at a temperature of about -10° C. to about 50° C., preferably about 0° C., over about 10 minutes to about 3 hours, preferably 1 hour. For example, 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,4-dihydroisoquinolinium chloride (34) is suspended in MeOH at 0° C., then treated with NaBH4 for about 1 hour to produce 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (1).
Sources & evidence
- ORD record
- ord-4d93d0d867f6416b8f41928248a53d6d
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04667038
Linked notes
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