HCID 86699763, compound → HCID 86699765, compound

HRID 515200Notes

Reaction equation

HRID 515200 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:7]=[C:8]([O:13][CH3:14])[C:9]=1[N+:10]([O-])=O)([CH3:3])=[CH2:2]>CO>[CH:1]([C:4]1[CH:5]=[C:6]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:7]=[C:8]([O:13][CH3:14])[C:9]=1[NH2:10])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 86699763HCID 86699763, compound

Product 1

HCID 86699765HCID 86699765, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(3-isopropenyl-5-methoxy-4-nitro-phenyl)-morpholine (3.0 g, 10.7 mmol) in methanol (170 ml) is degassed and flushed with argon for 20 min. To the reaction mixture is added 10% palladium on carbon (1.1 g) and the resulting mixture is hydrogenated in a par shaker (50 psi) for 16 h. After completion of reaction (monitored by TLC), the mixture is filtered through a pad of celite. The filtrate is concentrated in vacuo yielding (2-isopropyl-6-methoxy-4-morpholin-4-yl-phenyl)-amine. The crude material is used in the next step without further purification (2.3 g, 9.2 mmol, 86%).

Workup

  1. customflushed with argon for 20 min
  2. additionTo the reaction mixture is added 10% palladium on carbon (1.1 g)
  3. customAfter completion of reaction (monitored by TLC)
  4. filtrationthe mixture is filtered through a pad of celite
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-bc186510019a40fb9bfc0287b51565fc
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

Loading…