Tert-Butylamine → HCID 13748402, compound

HRID 1249620Notes

Reaction equation

HRID 1249620 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[N+:9]([O-:10])=[C:8]2[CH2:11][O:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:7]2=[CH:6][CH:5]=1.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22]>CO>[OH:1][CH:2]([C:4]1[N+:9]([O-:10])=[C:8]2[CH2:11][O:12][CH:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:14][C:7]2=[CH:6][CH:5]=1)[CH2:3][NH:25][C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 13340175HCID 13340175, compound

Product 1

HCID 13748402HCID 13748402, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 15.0 g. (0.055 mole) of 6-(1,2-epoxyethyl)-2-phenyl-4H-1,3-dioxino[5,4-b]pyridine N-oxide in 200 ml. of methanol was added 30 ml. tert-butylamine and the resulting reaction mixture was heated to the reflux temperature for 3 hours. Solvent and excess tertbutylamine were removed in vacuo to give 13.4 g. (73.6%) of 6-(1-hydroxy-2-tert-butylaminoethyl)-2-phenyl-4H-1,3-dioxino[5,4-b]pyridine N-oxide after recrystallization from ethyl acetate: m.p. 165°-168° C.

Workup

  1. temperaturewas heated to the reflux temperature for 3 hours
  2. customSolvent and excess tertbutylamine were removed in vacuo
  3. customto give 13.4 g
  4. custom(73.6%) of 6-(1-hydroxy-2-tert-butylaminoethyl)-2-phenyl-4H-1,3-dioxino[5,4-b]pyridine N-oxide after recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2163c0a9093441d8abee1cb7fe2ae2fa
Source dataset
uspto-grants-1986_12
Patent number
US04632992

Reaction notes

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