Ammonium Chloride → HCID 9865171, compound

HRID 2188370Notes

Reaction equation

HRID 2188370 reaction equation
[Mg].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br.[CH3:12][N:13]([CH:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=[O:22])[CH3:14].[Cl-:29].[NH4+]>CCOCC>[ClH:29].[CH3:14][N:13]([CH:15]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1([CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([O:3][CH3:2])[CH:5]=1)[OH:22])[CH3:12]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 40672073-Methoxybenzyl bromideHCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 9865171HCID 9865171, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

0.63 g (25.9 mmole) of magnesium turnings was stirred in 10 ml of ether of analysis purity. 5.21 g (25.9 mmole) of 3-methoxybenzyl bromide dissolved in 20 ml of ether were added dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was stirred for a further hour at RT. 5.0 g (21.6 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 were dissolved in 10 ml of ether, added dropwise to the Grignard reagent while cooling in an ice bath, and stirred for 15 hours at RT. The reaction solution was worked up by adding 40 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT, each time with 80 ml of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 7.53 g of crude base (98.6 of theory) were obtained. 4.45 g of 2-(dimethylaminophenylmethyl)-1-(3-methoxybenzyl)cyclohexanol, hydrochloride (52.8% of theory) were obtained from the crude base according to the procedure described in Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes when heated above 160° C.

Workup

  1. additionwere added dropwise so that the reaction mixture
  2. additionAfter completion of the addition the reaction mixture
  3. temperaturewhile cooling in an ice bath
  4. stirringstirred for 15 hours at RT
  5. temperaturewhile cooling in an ice bath
  6. extractionwas extracted three times at RT
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)
  10. custom7.53 g of crude base (98.6 of theory) were obtained

Sources & evidence

ORD record
ord-56d1d8d485174bbb916093193c65386d
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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