1-Iodonaphthalene → HCID 131723355, compound

HRID 2188409Notes

Reaction equation

HRID 2188409 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C([Mg][Cl:16])(C)C.[CH3:17][N:18]([CH:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=[O:27])[CH3:19].[Cl-].[NH4+]>CCOCC>[ClH:16].[CH3:19][N:18]([CH:20]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1)[OH:27])[CH3:17]

Participants

6

Reactant 4

HCID 70041-IodonaphthaleneHCID 25517Ammonium ChlorideHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanoneHCID 178418918HCID 178418918, compound

Product 1

HCID 131723355HCID 131723355, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-10 °C

Procedure

0.824 g (3.24 mmole) of 1-iodonaphthalene were dissolved in 2 ml of ether, cooled to −10° C., and 1.62 ml (3.24 mmole) of isopropylmagnesium chloride (2 M solution in tetrahydro-furan) were added dropwise. After stirring for one hour at 0° C., 0.50 g (2.16 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 and dissolved in 2 ml of ether were added dropwise, and the whole was stirred for 15 hours at RT. The reaction mixture was worked up by adding 2 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 5 ml of ether each time. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 1.00 g of crude base (129% of theory) was obtained, from which 0.23 g of 2-(dimethylaminophenylmethyl)-1-naphthalene-1-ylcyclohexanol, hydrochloride (17.9% of theory) having a melting point above 250° C. was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone.

Workup

  1. additionwere added dropwise
  2. stirringthe whole was stirred for 15 hours at RT
  3. temperaturewhile cooling in an ice bath
  4. extractionwas extracted three times at RT with 5 ml of ether each time
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-64383cf151f1429781663b42b228b59d
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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