Sodium Iodide → HCID 69420501, compound

HRID 459665Notes

Reaction equation

HRID 459665 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]1[CH:27]=[CH:26]C=C[C:21]=1[CH:22]=[O:23].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][CH:36]=[CH:37][C:38]=1[CH:12]([N:9]([CH3:7])[CH3:10])[CH:13]1[CH2:26][CH2:27][CH2:20][CH2:21][C:22]1=[O:23]

Participants

8

Reactant 6

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 69962-ChlorobenzaldehydeHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 707681-Pyrrolidino-1-cyclohexene

Product 1

HCID 69420501HCID 69420501, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

17.4 g (213 mmole) of freshly dried dimethylamine hydrochloride were added, while stirring, to 471 mg (469 mmole) sodium iodide solution (1 M in acetonitrile), which was cooled to 0° C. with an ice-bath; 60 ml (427 mmole) triethylamine and 60 ml (469 mmole) chlorotrimethylsilane were added dropwise, and the mixture was subsequently stirred at RT for one hour. While cooling with ice, 24 ml (213 mmole) 2-chlorobenzaldehyde were added, and stirring was continued at RT for a further hour. The mixture was cooled again to 0° C. with an ice-bath; 34 ml (213 mmole) 1-(pyrrolidino)-1-cyclohexene were added, and stirring was continued at RT for two hours. For working up, 300 ml half-concentrated hydrochloric acid were added to the mixture, while cooling with ice, and the mixture was stirred for 10 minutes, washed twice with 300 ml ether each time and rendered alkaline (pH approx. 9) with 770 ml dilute ammonia solution (5 vol. %). The mixture was extracted three times with 300 ml ether each time, and the combined organic extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator (500 to 10 mbar) without heat being supplied. 38.3 g 2-[(2-chlorophenyl) dimethylaminomethyl]cyclohexanone (68% of theoretical) were obtained in this manner.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas continued at RT for a further hour
  4. temperatureThe mixture was cooled again to 0° C. with an ice-bath
  5. stirringstirring
  6. waitwas continued at RT for two hours
  7. temperaturewhile cooling with ice
  8. stirringthe mixture was stirred for 10 minutes
  9. washwashed twice with 300 ml ether each time
  10. extractionThe mixture was extracted three times with 300 ml ether each time
  11. dry with materialthe combined organic extracts were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated on a rotary evaporator (500 to 10 mbar)
  14. temperaturewithout heat

Sources & evidence

ORD record
ord-98bf31adb83f435ca883ee5a641806c3
Source dataset
uspto-grants-2007_03
Patent number
USRE039530E1

Reaction notes

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