Sodium Hydroxide → HCID 15480564, compound

HRID 427260Notes

Reaction equation

HRID 427260 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[C:17]1([CH2:23][N:24]2[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH:27]1[CH2:26][CH2:25][N:24]([CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:29][CH2:28]1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 931882-(2-Nitrophenyl)anilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15480564HCID 15480564, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 30.0 g (0.140 mol) of 2-amino-2′-nitrobiphenyl and 111.5 g (0.630 mol) of 1-(phenylmethyl)-4-piperidone in 1200 mL of dichloromethane were added a total of 140.5 g (0.630 mol) of sodium triacetoxyborohydride in batches whilst maintaining a reaction temperature of 0° C. and the mixture was then stirred for 14 hours at room temperature. It was made alkaline with sodium hydroxide solution, the dichloromethane phase was separated off, dried over sodium sulfate and concentrated by evaporation. The residue was digested with methanol, then filtered. The filtrate was evaporated down, the residue remaining was purified by chromatography on aluminium oxide (activity stage 3) using PE/EE 9/1 (v/v) as eluant. Corresponding fractions were combined, freed from solvent and used in the next step without further purification. Yield: 40.0 g (74% of theory).

Workup

  1. customthe dichloromethane phase was separated off
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated by evaporation
  4. filtrationfiltered
  5. customThe filtrate was evaporated down
  6. customthe residue remaining was purified by chromatography on aluminium oxide (activity stage 3)
  7. customused in the next step without further purification

Sources & evidence

ORD record
ord-e7fe71fd3c6e49a3af1e24fa151f7e70
Source dataset
uspto-grants-2001_11
Patent number
US06313097B1

Reaction notes

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