Water → HCID 67763707, compound

HRID 362890Notes

Reaction equation

HRID 362890 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].O[N:8]=[C:9]1[CH2:14][CH2:13][N:12]([CH:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][O:18][C:17]3[CH:26]=[CH:27][C:28]([Br:30])=[CH:29][C:16]2=3)[CH2:11][CH2:10]1.O>C1COCC1.CCOCC>[NH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][O:18][C:17]3[CH:26]=[CH:27][C:28]([Br:30])=[CH:29][C:16]2=3)[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86753735HCID 86753735, compound

Product 1

HCID 67763707HCID 67763707, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Step 4): LiAlH4 (0.14 g, 3.7 mmol) was added to a solution of 11-(4-hydroxyiminopiperidin-1-yl)-2-bromo-6,11-dihydrodibenz[b,e]oxepin (1.5 g, 3.7 mmol) in dry THF (50 ml) under nitrogen atmosphere. The reaction mixture was heated at 60°-70° C. for 3 hours. After cooled at 0° C., the reaction mixture was hydrolyzed with water and diluted with ether, then filtered. The filtrate was concentrated to give 11-(4-aminopiperidin-1-yl)-2-bromo-6,11-dihydrodibenz[b,e]oxepin (69.1%): mp 142°-144° C.

Workup

  1. temperatureThe reaction mixture was heated at 60°-70° C. for 3 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0c74853528de45d4aeec5eb77d6d609d
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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