Phosphorus oxychloride → 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,4-dihydroisoquinolinium chloride

HRID 979370Notes

Reaction equation

[Cl-].C([C:5]1([CH2:20][CH2:21][CH2:22][C:23]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=2)([CH:26]([CH3:28])[CH3:27])[C:24]#[N:25])[CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([O:15][CH3:16])[CH:12]=2)[CH2:7][NH+:6]1[CH3:19])(O)=O.O=P(Cl)(Cl)[Cl:41]>>[Cl-:41].[CH3:38][O:37][C:31]1[CH:30]=[C:29]([C:23]([CH:26]([CH3:28])[CH3:27])([C:24]#[N:25])[CH2:22][CH2:21][CH2:20][C:5]2[CH2:14][C:13]3[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([O:15][CH3:16])[CH:12]=3)[CH2:7][N+:6]=2[CH3:19])[CH:34]=[CH:33][C:32]=1[O:35][CH3:36]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 179963103-carboxy-3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinolinium chloride

Product 1

HCID 867415383-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,4-dihydroisoquinolinium chloride

Procedure

The resulting salt of formula 33 is then decarboxylated to produce a dihydroisoquinolinium salt of formula 34 (step 5). For example, 3-carboxy-3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinolinium chloride (33) is treated with Et2N, followed by POCl3, to produce 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,4-dihydroisoquinolinium chloride (34).

Sources & evidence

ORD record: ord-6be5a1301fe24fd4a8050b41618d87f7
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04667038

Reaction notes

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