4-Methoxybenzylamine → HCID 117600113, compound

HRID 1497722Notes

Reaction equation

HRID 1497722 reaction equation
BrC1C=CC(O)=C(C(C2C=CC=CC=2)=O)C=1.COC1C=CC(CN)=CC=1.[Br:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([C:35](=[N:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH:35]([NH:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([O:50][CH3:51])=[CH:48][CH:49]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:29]=1

Participants

7

Reactant 5

HCID 754524-MethoxybenzylamineHCID 2290095-Bromo-2-hydroxybenzophenoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 136930497HCID 136930497, compound

Product 1

HCID 117600113HCID 117600113, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(5-Bromo-2-hydroxy-phenyl)-phenyl-methanone (5.0 g, 17.68 mmol) is dissolved in dichloromethane (20 mL). 4-Methoxybenzylamine (3.00 mL, 22.02 mmol) is added and the mixture stirred at room temperature for 2 hours. 4-Bromo-2-[(4-methoxy-benzylimino)-phenyl-methyl]-phenol (700 mg, 1.766 mmol) is dissolved in dichloromethane (6 mL) and treated with sodium triacetoxyborohydride (2.0 g, 8.96 mmol). The mixture is stirred at room temperature over the weekend. The mixture is poured into saturated aqueous sodium bicarbonate solution. The aqueous phase is exhaustively extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate, the drying agent is filtered off. The filtrate is concentrated to dryness in vacuo. The residue is purified by column chromatography on silica gel using dichloromethane as an eluant. The product fractions are evaporated to dryness in vacuo. This affordes the desired compound as a colourless oil.

Workup

  1. stirringThe mixture is stirred at room temperature over the weekend
  2. extractionThe aqueous phase is exhaustively extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationthe drying agent is filtered off
  5. concentrationThe filtrate is concentrated to dryness in vacuo
  6. customThe residue is purified by column chromatography on silica gel
  7. customThe product fractions are evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-402beafc869547df9e3745f83b4f7e86
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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