Formaldehyde → 4-(2-Nitrobutyl)morpholine

HRID 1391081Notes

Reaction equation

HRID 1391081 reaction equation
C=O.[CH2:3]([C:5]([N+:20]([O-:22])=[O:21])(CN1CCOCC1)[CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)[CH3:4]>>[N+:20]([CH:5]([CH2:3][CH3:4])[CH2:6][N:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 712Formaldehyde3×HCID 612794,4'-(2-Ethyl-2-nitrotrimethylene)dimorpholine

Product 1

HCID 624404-(2-Nitrobutyl)morpholine

Procedure

Formaldehyde, 37%, is added to the vessel with constant agitation and maintaining the temperature within the preferred 55°-60° C. range. The formaldehyde is added over a 21/2-6 hour addition period. Preferably, the formaldehyde is added in about 3-4 hours addition time. Addition times of less than 21/2 hours produce, 4,4'-(2-ethyl-2-nitrotrimethylene)dimorpholine and addition times of longer than 6 hours have no appreciable effect on product formation. Longer addition times than 6 hours and interruptions during addition produce no deleterious effects on the product quality or yield of the 2-nitrobutylmorpholine. The reaction mixture is held at the preferred temperature for a combined addition and holding period of 41/2-8 hours. Preferably, the reaction mixture is held for a minimum of two hours after the addition of the formaldehyde. During the holding period, the reaction goes to completion and any of the dimorpholine product formed converts to 2-nitrobutylmorpholine.

Workup

  1. temperaturemaintaining the temperature within the preferred 55°-60° C. range
  2. addition2-6 hour addition period
  3. additionaddition time
  4. additionAddition times of less than 21/2 hours
  5. customproduce
  6. additionLonger addition times than 6 hours
  7. additioninterruptions during addition

Sources & evidence

ORD record
ord-313019397c72402ba7f5c68a95ad86da
Source dataset
uspto-grants-1979_02
Patent number
US04140855

Reaction notes

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