4-(3,4-Dinitrobenzyl)morpholine → 4-(Morpholinomethyl)benzene-1,2-diamine

HRID 1946263Notes

Reaction equation

HRID 1946263 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O.[H][H]>[Pd]>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[C:16]([NH2:17])=[CH:15][CH:14]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 251933104-(3,4-Dinitrobenzyl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 251933094-(Morpholinomethyl)benzene-1,2-diamineYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
2.5 °C

Procedure

A mixture of 4-(3,4-dinitro-benzyl)-morpholine (1 mol. eq.) and 5% Pd/C (0.05 wt. eq.) in IMS (33 vol.) was stirred at 0-5° C. while the vessel was charged with hydrogen. The mixture was carefully warmed to 15-20° C. with stirring until the reaction was complete (<24 hours). The mixture was filtered and the filtrate evaporated to dryness to give 4-morpholin-4-ylmethyl-benzene-1,2-diamine (90%). The material was used immediately in the next step. (LC/MS (basic method): Rt 1.64, [M−N(CH2CH2)2O−]+ 121).

Workup

  1. temperatureThe mixture was carefully warmed to 15-20° C.
  2. stirringwith stirring until the reaction
  3. custom(<24 hours)
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-6c76694ed8d340f1b2679d908d2befe8
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

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