Hydrochloric Acid → HCID 67032498, compound

HRID 920555Notes

Reaction equation

HRID 920555 reaction equation
C(=[N:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[O:26][CH2:25][CH2:24][N:23]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22]2)=[CH:17][CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C1COCC1>[CH2:27]([N:23]1[CH2:24][CH2:25][O:26][CH:21]([C:18]2[CH:17]=[CH:16][C:15]([NH2:14])=[CH:20][CH:19]=2)[CH2:22]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86670013HCID 86670013, compound

Product 1

HCID 67032498HCID 67032498, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydrylidene-[4-(4-benzyl-morpholin-2-yl)-phenyl]-amine (3.30 g; 7.63 mmol) in THF (50 mL) was added hydrochloric acid (30.5 mL; 1.00 mol/L in water; 30.5 mmol). The resulting mixture was stirred overnight at RT. The reaction mixture was partitioned between 1M aqueous HCl and EtOAc. The aqueous layer was made basic with 1M aqueous NaOH (pH>10) and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to afford 4-(4-benzyl-morpholin-2-yl)-phenylamine (1.85 g).

Workup

  1. customThe reaction mixture was partitioned between 1M aqueous HCl and EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90935fdc5177416a9f626edc3a574365
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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