Sodium Carbonate → N-ethyl-N-[4-(3,4,5-trimethoxybenzoyloxy)butyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine

HRID 1732988Notes

Reaction equation

HRID 1732988 reaction equation
Cl.[CH2:2]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH2:6]1)[CH3:3].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28]I)=[O:23].C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C>[CH2:2]([N:4]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH2:6]1)[CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:22](=[O:23])[C:21]1[CH:30]=[C:31]([O:35][CH3:36])[C:32]([O:33][CH3:34])=[C:19]([O:18][CH3:17])[CH:20]=1)[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12843079N-ethyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine hydrochlorideHCID 128431604-Iodobutyl 3,4,5-trimethoxybenzoate

Product 1

HCID 12843161N-ethyl-N-[4-(3,4,5-trimethoxybenzoyloxy)butyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Using 2.0 g of N-ethyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine hydrochloride, 3.3 g of 4-iodobutyl 3,4,5-trimethoxybenzoate, 0.9 g of anhydrous sodium carbonate and 40 ml of methyl ethyl ketone, the free base, N-ethyl-N-[4-(3,4,5-trimethoxybenzoyloxy)butyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine, was obtained using the procedures described in Example 2 (ii). The free base was treated with methanesulfonic acid to obtain 1.5 g of N-ethyl-N-[4-(3,4,5-trimethoxybenzoyloxy)butyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine methanesulfonate as a pale-yellow oil.

Sources & evidence

ORD record
ord-94dcc5ea29784d6b87d80555a58690da
Source dataset
uspto-grants-1980_12
Patent number
US04239903

Reaction notes

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