Hydrochloric Acid → HCID 9800759, compound

HRID 2188397Notes

Reaction equation

HRID 2188397 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:17]([CH3:19])[CH3:18])[CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])=[CH:5][CH:4]=1.O.[CH2:21]([Mg]Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[ClH:2].[CH2:21]([C:11]1([OH:16])[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[CH:9]([C:6]1[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=1)[N:17]([CH3:19])[CH3:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 69943418HCID 69943418, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 9800759HCID 9800759, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The base was freed from 2.5 g (8.27 mmole) of the hydrochloride of 2-[(4-chlorophenyl)dimethylaminomethyl]cyclohexanone obtained according to stage 1 with 30 ml of water and 5 ml of amnonia solution (25 vol. %), was extracted three times with 30 ml of ether each time, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator without heating (500 to 10 mbar). 1.80 g (6.75 mmole) of this base were dissolved in 10 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 4.05 ml (8.13 mmole) of benzylmagnesium chloride (2 M solution in tetrahydro-furan), and stirred for 15 hours at RT. 2.30 g of crude base (94.9% of theory) were obtained, from which 1.24 g of 1-benzyl-2-[(4-chlorophenyl)dimethylaminomethyl]cyclohexanol, hydrochloride (46.7% of theory) were obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 130° C.

Workup

  1. customobtained
  2. extractionwas extracted three times with 30 ml of ether each time
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation on a rotary evaporator
  6. temperaturewithout heating (500 to 10 mbar)
  7. additionadded dropwise

Sources & evidence

ORD record
ord-5a3b05426e9145fc9b6033b7083bfc38
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

Loading…