Water → HCID 23457302, compound

HRID 1680175Notes

Reaction equation

HRID 1680175 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][C:5]1[N:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]2[C:12]([C:13]=1[CH3:14])=[CH:11][CH:10]=[CH:9][CH:8]=2.[BH4-].[Na+].B(F)(F)F.CCOCC.O>O1CCCC1>[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[CH:13]([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 23457299HCID 23457299, compound

Product 1

HCID 23457302HCID 23457302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 22.3 g of 2-(2-dimethylaminoethyl)-3-methyl-1-phenylindole in 160 ml of tetrahydrofuran there are added 6.1 g of sodium borohydride. 26.3 ml of boron trifluoride diethyl etherate are added dropwise at room temperature. The mixture is then heated at reflux for one hour, cooled to 0° and 15 ml of water are slowly added dropwise. The mixture is then poured onto ice-water and the resulting boron complex is extracted with ethyl acetate.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for one hour
  3. temperaturecooled to 0°
  4. additionThe mixture is then poured onto ice-water
  5. extractionthe resulting boron complex is extracted with ethyl acetate

Sources & evidence

ORD record
ord-89ccaeab3d9e49048c813464256b8776
Source dataset
uspto-grants-1981_06
Patent number
US04272533

Reaction notes

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