Hydrochloric Acid → HCID 86615025, compound

HRID 502501Notes

Reaction equation

HRID 502501 reaction equation
Cl.Cl.[CH3:3][N:4]([CH2:6][CH:7]1[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])([OH:17])[CH2:15][CH2:14][C:9]2(OCC[O:10]2)[CH2:8]1)[CH3:5].[CH3:25][S:26]([OH:29])(=[O:28])=[O:27]>O1CCCC1.O>[CH3:25][S:26]([OH:29])(=[O:28])=[O:27].[CH3:5][N:4]([CH2:6][CH:7]1[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])([OH:17])[CH2:15][CH2:14][C:9](=[O:10])[CH2:8]1)[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 68460215HCID 68460215, compound

Product 1

HCID 86615025HCID 86615025, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

178 ml of hydrochloric acid (32%, excess) were added rapidly at 0° C. to a solution of 7-dimethylaminomethyl-8-(2-methyl-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol hydrochloride (73.5 g, 215 mmol) in tetrahydrofuran/water mixture, and stirring was then carried out for 16 hours at RT. The mixture was adjusted to pH 12 with 32% sodium hydroxide solution, and extraction was carried out with ether. After evaporation of the solvent in vacuo, the residue was taken up in diisopropyl ether and EE, and the corresponding salt was precipitated by addition of methanesulfonic acid (13 ml, 200 mmol). 64.3 g (84%) of the product were obtained in the form of a colorless solid.

Workup

  1. extractionThe mixture was adjusted to pH 12 with 32% sodium hydroxide solution, and extraction
  2. customAfter evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-31dd413fbf824d7bb4711798767eed95
Source dataset
uspto-grants-2010_08
Patent number
US07776848B2

Reaction notes

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