HCID 449986, compound → HCID 449988, compound

HRID 864891Notes

Reaction equation

HRID 864891 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[N:9][CH2:10][CH2:11][N:12]([CH2:24][CH2:25][N:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34])[CH2:13][CH2:14][N:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].[BH4-].[Na+]>CO.C(Cl)Cl>[OH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][NH:15][CH2:14][CH2:13][N:12]([CH2:11][CH2:10][NH:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])[CH2:24][CH2:25][NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34]

Participants

5

Reactant 2

HCID 449986HCID 449986, compoundHCID 4311764Sodium borohydride

Product 1

HCID 449988HCID 449988, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N,N,N-tris[[[(2hydroxyphenyl)methylene]amino]ethyl]amine (40.0 g, 87 mmol) in 250 mL of methanol and 250 mL of methylene chloride was cooled in an ice bath. Sodium borohydride (10.0 g, 263 mmol) was added in several portions. Stirring was continued at room temperature for two hours. The solvents were evaporated and the residue was taken up in ether. This solution was washed with water and brine, dried over magnesium sulfate, filtered and evaporated to afford N,N,N-tris[[[(2-hydroxyphenyl)methyl]amino]ethyl]amine(30.0 g, 74%) as a colorless glass.

Workup

  1. customThe solvents were evaporated
  2. washThis solution was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a7ca8eb8f133473599556b61d8d60922
Source dataset
uspto-grants-1996_10
Patent number
US05565184

Reaction notes

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