Tert-Butylamine → HCID 15557357, compound

HRID 267803Notes

Reaction equation

HRID 267803 reaction equation
COC1C2OCC3(CO3)COC=2C=CC=1.C(N)(C)(C)C.C(O)(=O)/C=C\C(O)=O.C(O)(=O)/C=C\C(O)=O.[C:37]([NH:41][CH2:42][C:43]1([OH:56])[CH2:49][O:48][C:47]2[CH:50]=[CH:51][CH:52]=[C:53]([O:54][CH3:55])[C:46]=2[O:45][CH2:44]1)([CH3:40])([CH3:39])[CH3:38]>CO.C(OCC)(=O)C>[C:37]([NH:41][CH2:42][C:43]1([OH:56])[CH2:49][O:48][C:47]2[CH:50]=[CH:51][CH:52]=[C:53]([O:54][CH3:55])[C:46]=2[O:45][CH2:44]1)([CH3:40])([CH3:39])[CH3:38]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 444266Maleic AcidHCID 15557312HCID 15557312, compoundHCID 15557358HCID 15557358, compound

Product 1

HCID 15557357HCID 15557357, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of 6-methoxy-3,4-dihydro-2H-1,5-benzodioxepin-3-spiro-2'-oxirane (520 mg.; 2.5 mmole) in a mixture of tert-butylamine (548 mg.; 7.5 mmole) and methanol (4 ml.) is stirred at room temperature for 16 hours, by which time the solid dissolves, and reaction is complete as shown by thin layer chromatography (TLC). Evaporation of the solution yields 726 mg. of product in the form of an oil. A solution of the crude amine (698.5 mg.; 2.48 mmole) in ethyl acetate (7 ml.) is added to a hot solution of maleic acid (290 mg.; 2.5 mmole) in ethyl acetate (4 ml.). After allowing the mixture to stand for an hour at room temperature, the product is collected, washed with ethyl acetate and dried at 60°C. in air yielding 909 mg. (91.6%) of 3-tert-butylaminomethyl-3-hydroxy-6-methoxy-3,4-dihydro-2H-1,5-benzodioxepin hydrogen maleate, m.p. 188°-190.5°C. (dec.) after softening at ca. 184° C. Recrystallization from ethanol (16 ml.) provides 686 mg. (69.1%) of product, m.p. 193°-195° C. (dec.).

Workup

  1. dissolutiondissolves
  2. customreaction
  3. customEvaporation of the solution
  4. customyields 726 mg
  5. waitto stand for an hour at room temperature
  6. customthe product is collected
  7. washwashed with ethyl acetate
  8. customdried at 60°C. in air
  9. customyielding 909 mg
  10. customafter softening at ca. 184° C
  11. customRecrystallization from ethanol (16 ml.)
  12. customprovides 686 mg

Sources & evidence

ORD record
ord-dd2933d4477a4a478552a0bafbe58431
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

Loading…