Sodium borohydride → HCID 70233016, compound

HRID 1966483Notes

Reaction equation

HRID 1966483 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[CH:5][C:4]=1[N+:23]([O-])=O.[BH4-].[Na+]>CO.[O-]S([O-])(=O)=O.[Cu+2]>[NH2:23][C:4]1[CH:5]=[C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:16])[CH2:13][CH2:14]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70233138HCID 70233138, compound

Product 1

HCID 70233016HCID 70233016, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (4-(4-methoxy-3-nitrophenyl)piperazin-1-yl) (phenyl)methanone (3.41 g, 10 mmol) and 2M CuSO4 (0.160 g, 1 mmol) in methanol (50 mL), NaBH4 (1.89 g, 50 mmol) was added in portions at room temperature. After stirring it for 30 min, it was filtered through celite, filtrate was evaporated under vacuum. Flash column chromatography afforded (4-(3-amino-4-methoxyphenyl)piperazin-1-yl) (phenyl)methanone (2.7 g,) 87% yield. 1H NMR (500 MHz, CDCl3): δ 3.0 (bs, 2H), 3.15 (bs, 2H), 3.59 (bs, 2H), 3.84 (s, 5H), 3.98 (bs, 2H), 6.34 (dd, J=2.8 Hz, 1H), 6.43 (d, J=2.7 Hz, 1H), 6.75 (d, J=8.6 Hz, 1H), 7.45 (m, 5H). 13C NMR (500 MHz, CDCl3): δ 42.4, 48.0, 56.3, 51.2, 51.5, 56.1, 105.9, 107.1, 111.3, 127.3, 128.7, 129.9, 135.9, 136.9, 142.6, 146.0, 170.5.

Workup

  1. filtrationit was filtered through celite, filtrate
  2. customwas evaporated under vacuum

Sources & evidence

ORD record
ord-f8198d092cf2453ba37ca60dd3fec5c8
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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