2,3-Dihydro-α-methyl-N-(phenylmethyl)-1,4-benzodioxin-2-methanamine → HCID 23347142, compound

HRID 1855961Notes

Reaction equation

HRID 1855961 reaction equation
[CH2:1]([NH:8][CH:9]([CH:11]1[O:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12]1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:38])[CH2:36]Br)=[CH:31][C:30]=1[S:39]([NH2:42])(=[O:41])=[O:40])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(C(C)=O)C>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:38])[CH2:36][N:8]([CH:9]([CH:11]2[O:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][CH2:12]2)[CH3:10])[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:31][C:30]=1[S:39]([NH2:42])(=[O:41])=[O:40])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 5418362,3-Dihydro-α-methyl-N-(phenylmethyl)-1,4-benzodioxin-2-methanamineHCID 12232709HCID 12232709, compound

Product 1

HCID 23347142HCID 23347142, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 10.76 g (0.04 mole) of N-benzyl-1-(1,4-benzodioxan-2-yl)ethylamine (i1 '), 7.68 g (0.02 mole) of 2-benzyloxy-5-bromoacetylbenzenesulfonamide, and 50 ml of methyl ethyl ketone was reluxed for 2 hours with stirring and then methyl ethyl ketone was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted using a mixture of chloroform and ethyl acetate of 2:1 by volume ratio to provide 9.6 g of the isomer (i1 ') of crude 2-benzyloxy-5-[N-benzyl-1-(1,4-benzodioxan-2-yl)ethylaminoacetyl]benzenesulfonamide.

Workup

  1. distillationmethyl ethyl ketone was distilled off under reduced pressure
  2. washeluted
  3. additiona mixture of chloroform and ethyl acetate of 2:1 by volume ratio

Sources & evidence

ORD record
ord-ef5c55acb1b64e60bc699cc72b00dc1c
Source dataset
uspto-grants-1980_08
Patent number
US04217305

Reaction notes

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