3,4,5-Trimethoxybenzoic Acid → HCID 68681845, compound

HRID 1992745Notes

Reaction equation

HRID 1992745 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][CH2:16][NH:17][CH2:18][C:19]([CH3:27])=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([O:41][CH3:42])[C:38]=1[O:39][CH3:40])[C:33](O)=[O:34].S(Cl)(Cl)=O>C(N(CC)CC)C>[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][CH2:16][N:17]([CH2:18][C:19]([CH3:27])=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:33](=[O:34])[C:32]2[CH:31]=[C:30]([O:29][CH3:28])[C:38]([O:39][CH3:40])=[C:37]([O:41][CH3:42])[CH:36]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 24386Thionyl ChlorideHCID 68683724HCID 68683724, compound

Product 1

HCID 68681845HCID 68681845, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Experimental condition similar to Example 18 were used with [3-(S)-(3-benzyl-piperazin-1-yl)-propyl]-(2-methyl-3-phenyl-allyl)-amine (prepared from (S)-2-benzyl piperazine described on scheme 11) 0.08 g (0.24 mmol), 3,4,5-trimethoxy benzoic acid 0.05 g (0.24 mmol), thionyl chloride 0.02 ml (0.46 mmol) and triethylamine. The free amine after purification was transformed to HCl salt, yielding 45 mg of a brown, semi-solid salt. Yield: 7%.

Workup

  1. customThe free amine after purification
  2. customyielding 45 mg of a brown, semi-solid salt

Sources & evidence

ORD record
ord-1a051fc26d6147b5acb67b323b3fb960
Source dataset
uspto-grants-2010_01
Patent number
US07649011B2

Reaction notes

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