Sodium metaborate → 4-{N-[4-(3-nitrophenyl)-2-butyl]-aminomethyl}-2,2-dimethylchroman

HRID 542897

Reaction equation

HRID 542897 reaction equation
[NH2:1][CH:2]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)[CH3:3].[CH3:15][C:16]1([CH3:28])[CH2:25][CH:24]([CH:26]=O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:17]1.B([O-])=O.[Na+]>CO>[N+:12]([C:8]1[CH:7]=[C:6]([CH2:5][CH2:4][CH:2]([NH:1][CH2:26][CH:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:17][C:16]([CH3:15])([CH3:28])[CH2:25]2)[CH3:3])[CH:11]=[CH:10][CH:9]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 145326Sodium metaborateHCID 135370432,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-4-carbaldehydeHCID 135370444-(3-Nitrophenyl)butan-2-amine

Product 1

HCID 135370454-{N-[4-(3-nitrophenyl)-2-butyl]-aminomethyl}-2,2-dimethylchroman

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12.1 g (0.1 mol) of 2-amino-4-(3-nitrophenyl)butane are added to 19.0 g (0.1 mol) of 2,2-dimethyl-4-formyl-chroman in 100 ml of methanol at 20° C., with stirring and slight cooling, and the mixture is stirred for 1.5 hours. Thereafter, 4.5 g of sodium boranate are added, and stirring is continued for 1 day, and the mixture is evaporated down and worked up with ethyl acetate/water. The ethyl acetate phase is washed with water, dried and evaporated down. Distillation gives 4-{N-[4-(3-nitrophenyl)-2-butyl]-aminomethyl}-2,2-dimethylchroman. B.p.: 225°-235° C./0.04 mmHg.

Workup

  1. stirringslight cooling, and the mixture is stirred for 1.5 hours
  2. stirringstirring
  3. customthe mixture is evaporated down
  4. washThe ethyl acetate phase is washed with water
  5. customdried
  6. customevaporated down
  7. distillationDistillation

Sources & evidence

ORD record
ord-551240f347614c54874b79a1bb7ff07d
Source dataset
uspto-grants-1987_04
Patent number
US04659737

Linked notes

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