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

HRID 979368Notes

Reaction equation

[C:1]([C:6]1([CH2:21][CH2:22][CH2:23][C:24]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=2)([CH:27]([CH3:29])[CH3:28])[C:25]#[N:26])[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=2)[CH2:8][N:7]1[CH3:20])([O:3]CC)=[O:2].[ClH:40]>>[Cl-:40].[C:1]([C:6]1([CH2:21][CH2:22][CH2:23][C:24]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=2)([CH:27]([CH3:29])[CH3:28])[C:25]#[N:26])[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=2)[CH2:8][NH+:7]1[CH3:20])([OH:3])=[O:2]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 202022283-carboethoxy-3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

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

Procedure

The resulting alkylated ester of formula 32 is then hydrolyzed by warming it in 6N HCl to produce a carboxylic acid/ammonium salt of formula 33 (step 4). For example, 3-carboethoxy-3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (32) is heated at 35° C. in 6N HCl to produce 3-carboxy-3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinolinium chloride (33).

Sources & evidence

ORD record: ord-96dc3701217d454eb9357ebb9da8a3c0
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04667038

Reaction notes

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