Tetrahydrofuran → HCID 21474842, compound

HRID 2294274Notes

Reaction equation

HRID 2294274 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:3]=1[O:4][CH2:5][CH:6]([NH:8][C:9](=O)[CH3:10])[CH3:7].O1CCCC1.[ClH:22].C(O)C>C(OCC)C>[ClH:22].[CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:3]=1[O:4][CH2:5][CH:6]([NH:8][CH2:9][CH3:10])[CH3:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 567741Mexiletine acetateHCID 21887872Ethanol hydrochloride

Product 1

HCID 21474842HCID 21474842, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Borane-dimethylsulfide complex (10-10.2M, 35 ml, 1.2 eq) was added to a refluxing solution of N-[2-(2,6-dimethylphenoxy)-1-methylethyl]-acetamide (68 g, 0.289 mol) and tetrahydrofuran (400 ml) under a nitrogen atmosphere. After the addition was complete, the reaction was allowed to reflux for 25 hours. The reaction was then cooled to room temperature and 10% hydrochloric acid/ethanol was added until the mixture was acidic. After concentration of the reaction mixture, ethyl ether was added to induce crystallization. The solids were isolated by filtration and dried to give [2-(2,6-dimethylphenoxy)-1-methylethyl]-ethylamine hydrochloride salt (53.0 g, 75% yield, mp 184.7-185.8° C.).

Workup

  1. additionAfter the addition
  2. temperatureto reflux for 25 hours
  3. customcrystallization
  4. customThe solids were isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-dc12d99de32c47509e1ca68059e36207
Source dataset
uspto-grants-1997_11
Patent number
US05688830

Reaction notes

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