Tert-Butylamine → HCID 70454632, compound

HRID 1249623Notes

Reaction equation

HRID 1249623 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]2[O:18][CH2:17]2)=[N+:13]([O-:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]([OH:18])[CH2:17][NH:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[N+:13]([O-:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 13340172HCID 13340172, compound

Product 1

HCID 70454632HCID 70454632, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.50 g. (0.0042 mole) of [5-benzyloxy-2-(1,2-epoxyethyl)pyridine N-oxide] in 20 ml. of methanol was added 0.5 ml. tert-butylamine and the resulting mixture heated to the reflux temperature for 4 hours. Solvent and excess tert-butylamine were removed in vacuo to give 280 mg. (43%) of the desired product after recrystallization from ether/ethyl acetate; m.p. 148°-150° (dec.). Mass spec (70 eV) m/e 300 (M-16), m/e 243 [MH2NC(CH3)3); NMR (DMSO d6)delta 7.90 (d, 1H, H6), 7.30 (m, 6H, benzyl C6H5 and H4), 7.00 (m, 1H, H3), ##STR14## and 1.13 [s, 9H, C(CH3 ]; ir (KBr) 1171 (N+ -O-).

Workup

  1. customSolvent and excess tert-butylamine were removed in vacuo
  2. customto give 280 mg
  3. custom(43%) of the desired product after recrystallization from ether/ethyl acetate

Sources & evidence

ORD record
ord-aff0962e1f6747aca19b6d5bc1ec0d32
Source dataset
uspto-grants-1986_12
Patent number
US04632992

Reaction notes

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