Tetrahydrofuran → HCID 68553772, compound

HRID 2244497Notes

Reaction equation

HRID 2244497 reaction equation
C(CN[C:6]1([C:16]#[N:17])[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)C=C.[CH2:18]([Mg]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+].[CH2:29]1[CH2:33]OC[CH2:30]1>>[CH2:33]([NH:17][CH2:16][C:6]1([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7][CH2:8][C:9]2([O:10][CH2:11][CH2:12][O:13]2)[CH2:14][CH2:15]1)[CH:29]=[CH2:30]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 68554501HCID 68554501, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 68553772HCID 68553772, compound

Procedure

A solution of 3.50 g 8-(allylmethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile in 35 ml analytical grade tetrahydrofuran was added dropwise to 14.8 ml 2.0 molar benzylmagnesium chloride solution in THF under a nitrogen atmosphere and the mixture was stirred overnight at room temperature. For working up, 25 ml saturated ammonium chloride solution were added, while cooling with ice, the phases were separated, the aqueous phase was extracted three times with 25 ml diethyl ether each time, the combined organic phases were dried over sodium sulfate, filtered and concentrated and the residue was largely freed from solvent residues in vacuo. The crude allyl-(8-benzyl-1,4-dioxaspiro[4.5]dec-8-yl)methylamine obtained (5.41 g) was stirred, without further purification, with a mixture of 13 ml conc. hydrochloric acid (32 per cent by weight) and 7.5 ml water for 24 hours at room temperature. The reaction mixture was then first washed three times with 50 ml diethyl ether each time and then rendered alkaline by addition of sodium hydroxide solution (32 per cent by weight), while cooling with ice, and extracted three times with 100 ml methylene chloride each time, the combined methylene chloride extracts were dried over sodium sulfate, filtered and concentrated and the residue was largely freed from solvent residues in vacuo. 3.55 g 4-(allylmethylamino)-4-benzylcyclohexanone were obtained.

Workup

  1. temperaturewhile cooling with ice
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted three times with 25 ml diethyl ether each time
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03c83e4bf29d4fcba8d3aeafbc76de83
Source dataset
uspto-grants-2010_03
Patent number
US07678834B2

Reaction notes

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