Borane → HCID 21428691, compound

HRID 437564Notes

Reaction equation

HRID 437564 reaction equation
B.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=O)[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=O)=[CH:3]1>O1CCCC1.CCOCC>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][CH:17]2[CH2:16][CH2:15][N:14]([CH2:12][CH2:11][C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[NH:2][CH:3]=3)[CH2:19][CH2:18]2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 6331BoraneHCID 214286971-[4-(4-Chlorophenoxy)-1-piperidinyl]-2-(1H-indol-3-yl)-1,2-ethanedione

Product 1

HCID 21428691HCID 21428691, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

60 ml. of a 1M solution of boron trihydride in tetrahydrofuran are added dropwise to a stirred solution of 7.0 g of 1-(indol-3-ylglyoxyloyl)-4-(p-chlorophenoxy)piperidine in 135 ml. of tetrahydrofuran under nitrogen. The solution is stirred at ambient temperature for 18 hours and the tetrahydrofuran is removed under reduced pressure to give a white boron complex. The complex is destroyed by refluxing in 135 ml. of methanol with a few drops of glacial acetic acid. After cooling, the methanol is removed under reduced pressure to give a yellow oil. The oil is dissolved in ether, the ether is washed with water, dried and removed under reduced pressure to give a yellow oil. After standing under vacuum for a week, the oil crystallizes to a yellow solid. The solid is recrystallized from toluene and then from an ethanol and water mixture to give white crystals of 3-{2-[4-(p-chlorophenoxy)piperidyl]ethyl}indole, m.p. 132°-133° C.

Workup

  1. customthe tetrahydrofuran is removed under reduced pressure
  2. customto give a white boron complex
  3. customThe complex is destroyed
  4. temperatureby refluxing in 135 ml
  5. temperatureAfter cooling
  6. customthe methanol is removed under reduced pressure
  7. customto give a yellow oil
  8. washthe ether is washed with water
  9. customdried
  10. customremoved under reduced pressure
  11. customto give a yellow oil
  12. waitAfter standing under vacuum for a week
  13. customthe oil crystallizes to a yellow solid
  14. customThe solid is recrystallized from toluene

Sources & evidence

ORD record
ord-e824c3f1df1f4bb5a9e8128b83afe137
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

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