Ethylenediamine → N-(3,5-Difluorobenzyl)ethylenediamine

HRID 2352234Notes

Reaction equation

HRID 2352234 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.[CH2:11]([NH2:14])[CH2:12][NH2:13].[BH4-].[Na+].C(NCCN)C1C=CC=CC=1>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH:13][CH2:12][CH2:11][NH2:14]

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 77801N-BenzylethylenediamineHCID 5881603,5-DifluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 14653371N-(3,5-Difluorobenzyl)ethylenediamineYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 16.77 g (0.118 mol) quantity of 3,5-difluorobenzaldehyde was treated with 50 ml ethylenediamine and 4.47 g (0.118 mol) sodium borohydride in 500 ml methanol by the method prescribed for N-benzylethylenediamine (Example 1) to give 12.0 g (55% yield) of desired product, b.p. 90°-92° C. at 199.98-226.65 Nm-2.

Sources & evidence

ORD record
ord-bc21e46a188f4b1785cd78c921e72997
Source dataset
uspto-grants-1989_10
Patent number
US04876266

Reaction notes

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