Sodium Iodide → HCID 69943418, compound

HRID 2188396Notes

Reaction equation

HRID 2188396 reaction equation
[ClH:1].CNC.[I-].[Na+].[CH2:7]([N:9]([CH2:12][CH3:13])[CH2:10]C)C.Cl[Si](C)(C)C.Cl[C:20]1C=C[C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.N1([C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)CCCC1>Cl>[Cl:1][C:33]1[CH:34]=[CH:35][C:36]([CH:12]([N:9]([CH3:7])[CH3:10])[CH:13]2[CH2:20][CH2:21][CH2:22][CH2:23][C:24]2=[O:25])=[CH:37][CH:38]=1

Participants

8

Reactant 6

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 77264-ChlorobenzaldehydeHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 707681-Pyrrolidino-1-cyclohexene

Product 1

HCID 69943418HCID 69943418, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

15.1 g (185 mmole) of freshly dried dimethylamine hydrochloride were added while stirring to 407 ml (407 mmole) of sodium iodide solution (1 M in acetonitrile) cooled to 0° C. in an ice bath, following which 52 ml (370 mmole) of triethylamine and 52 ml (407 mmole) of chlorotrimethylsilane were added dropwise and the whole was stirred for a further hour at RT. 26.0 g (185 mmole) of 4-chlorobenzaldehyde were added while cooling with ice, and the whole was stirred for a further hour at RT. The reaction mixture was cooled again to 0° C. with an ice bath, 12.0 ml (185 mmole) of 1-(pyrrolidino)-1-cyclohexene were added, and the whole was stirred for a further two hours at RT. The reaction mixture was worked up by adding 280 ml of semi-concentrated hydrochloric acid while cooling in an ice bath, stirred for 10 minutes, washed twice with 280 ml of ether each time, and then adjusted to the alkaline range (pH ca. 9) with 700 ml of dilute amnmonia solution (5 vol. %). The reaction mixture was extracted three times with 280 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). 16.2 g of crude base (33.0% of theory) were obtained, from which 14.8 g of the hydrochloride of 2-[(4-chlorophenyl)dimethylaminomethyl]cyclohexanone (57.2% of theory) were obtained according to the procedure described in Example 1 (2nd Stage) with chlorotrimethylsilane/water in 2-butanone.

Workup

  1. additionwere added dropwise
  2. temperaturewhile cooling with ice
  3. stirringthe whole was stirred for a further hour at RT
  4. temperatureThe reaction mixture was cooled again to 0° C. with an ice bath
  5. stirringthe whole was stirred for a further two hours at RT
  6. temperaturewhile cooling in an ice bath
  7. stirringstirred for 10 minutes
  8. washwashed twice with 280 ml of ether each time
  9. extractionThe reaction mixture was extracted three times with 280 ml of ether each time
  10. dry with materialthe combined organic extracts were dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated by evaporation on a rotary evaporator
  13. temperaturewithout heating (500 to 10 mbar)

Sources & evidence

ORD record
ord-cbf3cfbf14cd4565934a13a5ce3ad79a
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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