Methanol → HCID 15592114, compound

HRID 2417597Notes

Reaction equation

HRID 2417597 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[C:20](=[O:26])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:15][CH2:14]2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br.CO>C(Cl)Cl.C(=O)=O>[OH:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([C:19]3[C:20](=[O:26])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:17][CH2:18]2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 15592113HCID 15592113, compound

Product 1

HCID 15592114HCID 15592114, compound

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-[4-[2-(3,4-dimethoxyphenyl)ethyl]-1-piperazinyl]-2,4,6-cycloheptatrien-1-one (1.10 g, described in Example 4) in methylene chloride (5 ml) was cooled to -65° C. in dry ice bath. A solution of boron tribromide (3.36 g) in methylene chloride (5 ml) was added dropwise to the solution of the compound. After the addition, the temperature was allowed to rise to room temperature. After 4 hr, the mixture was cooled in an ice bath and methanol (20 ml) was added dropwise. The resulting mixture was slowly brought to reflux and the solid was allowed to dissolve. The solution was then concentrated to the point at which crystals start to separate. Some diethyl ether was added, the mixture was cooled overnight, and filtered to give crude product (1.4 g). Recrystallization form methanol gave the hydrobromide salt (0.5 g) of the title compound: mp 256°-258° C.; ir(nujol) 3490, 2540 and 1522 cm-1 ; uv max(MeOH) 342 (ε=7820), 250 (ε=10720) and 222 nm(ε=11535); nmr(DMSO-d6)δ3.25 (m, 12H), 6.8 (m, 7H) and 8.7 (broad, 2H); and Anal. Calcd for C19H22N2O3.HBr: C, 56.02% H, 5.69% N, 6.88% and Found: C, 55.91% H, 5.74% N, 6.86%.

Workup

  1. additionAfter the addition
  2. customto rise to room temperature
  3. temperaturethe mixture was cooled in an ice bath
  4. temperatureto reflux
  5. dissolutionto dissolve
  6. concentrationThe solution was then concentrated to the point at which crystals
  7. customto separate
  8. additionSome diethyl ether was added
  9. temperaturethe mixture was cooled overnight
  10. filtrationfiltered
  11. customto give crude product (1.4 g)
  12. customRecrystallization
  13. customform methanol

Sources & evidence

ORD record
ord-b5349abb6ac34f798dd15d6784165f37
Source dataset
uspto-grants-1984_09
Patent number
US04469693

Reaction notes

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