Dichloromethane → 2-Morpholin-4-yl-indan-5-ylamine

HRID 418361Notes

Reaction equation

HRID 418361 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[CH2:7]2)([O-])=O.C(Cl)Cl>CO.[Pd]>[N:13]1([CH:8]2[CH2:7][C:6]3[C:10](=[CH:11][CH:12]=[C:4]([NH2:1])[CH:5]=3)[CH2:9]2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 591907584-(5-Nitro-indan-2-yl)-morpholine

Product 1

HCID 591908752-Morpholin-4-yl-indan-5-ylamineYield 101.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(5-nitro-indan-2-yl)-morpholine (210 mg, 0.85 mmol) in 20 mL of methanol was added Pd/C 10% (20 mg). The mixture was placed under a H2 atmosphere with stirring for 2 h. TLC showed 2 spots. CH2Cl2 was added to dissolve the ppt. that had formed and the hydrogenation continued further 2 h. The catalyst was removed by filtering, and the filtrate evaporated to give 188 mg of 2-morpholin-4-yl-indan-5-ylamine. The crude amine was used in the next step without purification.

Workup

  1. dissolutionto dissolve the ppt
  2. customthat had formed
  3. waitthe hydrogenation continued further 2 h
  4. customThe catalyst was removed
  5. filtrationby filtering
  6. customthe filtrate evaporated

Sources & evidence

ORD record
ord-d4727b3e0ae345afb637f6fe94745554
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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