Formic Acid → Bmy 25368

HRID 1651348Notes

Reaction equation

HRID 1651348 reaction equation
[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(O)=O.O>C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:14]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 8082PiperidineHCID 230519081-Amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dione

Product 1

HCID 135156Bmy 25368Yield 62.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 1-amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dione (6.0 g, 21.8 mmole) in 150 mL of toluene was treated with piperidine (4.3 mL, 3.7 g, 43.6 mmole) and the mixture was heated to 65° C., and then cooled to about 30° C. Formic acid (2.2 mL of 95% aqueous formic acid containing 2.5 g formic acid, 55.4 mmole) was added. The mixture was heated to reflux temperature and the water formed was collected by azeotropic distillation. When the distillate became clear and gas evolution had ceased (about 30 minutes at reflux), the mixture was cooled and the solids were collected by filtration, washed with toluene, methanol and dried to yield 4.7 g (62.8%) of the title compound; mp=223°-228° C.

Workup

  1. temperaturecooled to about 30° C
  2. temperatureThe mixture was heated
  3. temperatureto reflux temperature
  4. distillationwas collected by azeotropic distillation
  5. temperature(about 30 minutes at reflux)
  6. temperaturethe mixture was cooled
  7. filtrationthe solids were collected by filtration
  8. washwashed with toluene, methanol
  9. customdried

Sources & evidence

ORD record
ord-b9cfc6c9c64f4c8f960bb37205dd4378
Source dataset
uspto-grants-1990_05
Patent number
US04927968

Reaction notes

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