Hydrochloric Acid → 3-Ethyl-3-(3-methoxyphenyl)azepan-2-one

HRID 2049337Notes

Reaction equation

HRID 2049337 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1.[CH:17]([N-]C(C)C)(C)[CH3:18].[Li+].C(Br)C.Cl>O1CCCC1>[CH2:17]([C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:10]1=[O:16])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 2724682Lithium diisopropylamideHCID 12875111Hexahydro-3-(3-methoxyphenyl)-2H-azepin-2-one

Product 1

HCID 28154553-Ethyl-3-(3-methoxyphenyl)azepan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexahydro-3-(3-methoxyphenyl)-2H-azepin-2-one (2.19 g) in dry tetrahydrofuran was added to a stirred solution of lithium diisopropylamide (from butyllithium 1.4 molar 15.7 ml, and diisopropylamine 3.15 ml) under nitrogen at 0° C. Ethyl bromide (1 ml) was added in one portion and the reaction allowed to warm up to room temperature. After two hours the reaction was poured into 2 M HCl, the organic layer separated and the aqueous layer extracted with chloroform. The combined organic layers were dried over magnesium sulphate, filtered and evaporated to an oil which was crystallised from ethyl acetate giving 1.68 g of the title compound m.p. 85°-7° C.

Workup

  1. customthe organic layer separated
  2. extractionthe aqueous layer extracted with chloroform
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to an oil which
  6. customwas crystallised from ethyl acetate giving 1.68 g of the title compound m.p. 85°-7° C.

Sources & evidence

ORD record
ord-78cda70d79e94ff88c60ae155e2e86eb
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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