Triethylamine → Triethylamine hydrochloride

HRID 1978408Notes

Reaction equation

HRID 1978408 reaction equation
CS(O[CH2:6][C@H:7]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][CH2:8]1)(=O)=O.[ClH:17].Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([CH2:25][NH:26][C:27]([C:29]2[S:39][C:38]3[N:40]4[C:31](=[CH:32][N:33]=[C:34]4[CH:35]=[CH:36][CH:37]=3)[CH:30]=2)=[O:28])[CH2:21][CH2:20]1.[CH2:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])[CH3:42]>C(O)C>[O:12]1[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][CH2:8][C@H:7]1[CH2:6][N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][NH:26][C:27]([C:29]2[S:39][C:38]3[N:40]4[C:31](=[CH:32][N:33]=[C:34]4[CH:35]=[CH:36][CH:37]=3)[CH:30]=2)=[O:28])[CH2:21][CH2:20]1.[ClH:17].[CH2:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])[CH3:42]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11128529(S)-(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl methanesulfonateHCID 21993937N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 2

HCID 11130Triethylamine hydrochlorideHCID 9804407(R)-N-[1-(1,4-benzodioxan-2-ylmethyl)piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the above crude (S)-2-methanesulfonyloxymethyl-1,4-benzodioxane, 1.05 g (2.71 mM) of N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride, and 1.20 ml (8.64 mM) of triethylamine in 30 ml of ethanol was refluxed for 3 days. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate-methanol=4/1 to 3/1) to provide the title compound and triethylamine hydrochloride as a mixture. This mixture was diluted with ethyl acetate and washed serially with aqueous solution of sodium hydrogen carbonate, water, and saturated aqueous solution of NaCl. The organic layer was dried over MgSO4 and the solvent was distilled off to provide the title compound.

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate-methanol=4/1 to 3/1)

Sources & evidence

ORD record
ord-c467df2bb67546778ec33b7939480055
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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