Borane → HCID 21428727, compound

HRID 437565Notes

Reaction equation

HRID 437565 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][CH:24]=[C:23]([Cl:27])[CH:22]=3)[CH2:16][CH2:15]2)=O)=[CH:3]1>O1CCCC1>[Cl:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[O:20][CH:17]1[CH2:16][CH2:15][N:14]([CH2:12][CH2:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:2][CH:3]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 21428721HCID 21428721, compound

Product 1

HCID 21428727HCID 21428727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

49 ml. of a 1M solution of boron trihydride in tetrahydrofuran are added dropwise to a stirred suspension of 5.3 g of 1-(indol-3-ylglyoxyloyl)-4-(m-chlorophenoxy)piperidine in 100 ml. of tetrahydrofuran under nitrogen. After an initial evolution of gas, the solution turns yellow and is stirred at ambient temperature for 13 hours. The tetrahydrofuran is removed under reduced pressure to give a solid white borane complex. The complex is destroyed by refluxing in 100 ml. of methanol with several drops of glacial acetic acid for one hour. After cooling, the methanol is removed under reduced pressure, leaving a yellow oil. The oil is evacuated at about 3 mm. for 72 hours and a gummy solid forms. The solid is recrystallized from acetonitrile and then from an ethanol and water mixture to give white microcrystals of 3{2-[4-(m-chlorophenoxy)piperidyl]ethyl}indole, m.p. 120°-123° C.

Workup

  1. customThe tetrahydrofuran is removed under reduced pressure
  2. customto give a solid white borane complex
  3. customThe complex is destroyed
  4. temperatureby refluxing in 100 ml
  5. waitof methanol with several drops of glacial acetic acid for one hour
  6. temperatureAfter cooling
  7. customthe methanol is removed under reduced pressure
  8. customleaving a yellow oil
  9. customThe oil is evacuated at about 3 mm
  10. waitfor 72 hours
  11. customThe solid is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-15321044c70442ad956a5da966212746
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

Loading…