Ethyl Bromide → HCID 20344789, compound

HRID 2049332Notes

Reaction equation

HRID 2049332 reaction equation
C([N-][CH:5]([CH3:7])C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C.CO[C:23]1[CH:24]=[C:25]([CH:29]2[CH2:35][CH2:34][CH2:33][CH2:32][N:31](C)[C:30]2=[O:37])[CH:26]=[CH:27][CH:28]=1.C(Br)C.C1C[O:44][CH2:43]C1>CCCCCC>[CH2:5]([C:29]1([C:25]2[CH:24]=[CH:23][CH:28]=[CH:27][C:26]=2[O:44][CH3:43])[CH2:35][CH2:34][CH2:33][CH2:32][NH:31][C:30]1=[O:37])[CH3:7]

Participants

8

Reactant 6

HCID 6332Ethyl BromideHCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 2727906hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-oneHCID 178418339Butyllithium

Product 1

HCID 20344789HCID 20344789, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Lithium diisopropylamide, prepared by adding 15% butyl lithium in hexane (15.7 ml) to diisopropylamine (3.15 ml) at -10° C. under nitrogen, was treated with a solution of hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one in THF. After 30 minutes, ethyl bromide (1.0 ml) was added. The mixture was allowed to warm to ambient temperature. After a further 2 hours the reaction was quenched with water. The organic layer was evaporated to give an oil that crystallised on scratching. The solid was recrystallised from ethyl acetate to give the title compound (1.68 g) m.p. 85°-87° C.

Workup

  1. customAfter a further 2 hours the reaction was quenched with water
  2. customThe organic layer was evaporated
  3. customto give an oil that
  4. customcrystallised
  5. customThe solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-11d699669cd74491a00fe9e4f41439f3
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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