Dichloromethane → HCID 67451092, compound

HRID 595345Notes

Reaction equation

HRID 595345 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=1)=[O:4].[CH2:23]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:24]1([CH2:23][N:30]([CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:6]=2)=[O:4])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7656DibenzylamineHCID 10340Sodium CarbonateHCID 86676533HCID 86676533, compound

Product 1

HCID 67451092HCID 67451092, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-bromo-1-[3-({3-[(phenylmethyl)oxy]propyl}oxy)phenyl]ethanone (13.17 g), dibenzylamine (6.4 g) and dichloromethane (25 mL) was added a solution of sodium carbonate (7.6 g) in water (50 mL). The reaction mixture was stirred at ambient temperature overnight. The organic layer was separated and concentrated to a minimum and tert-butyl methyl ether was added. The organic layer was washed with dilute acetic acid (4 times) and 0.1N sodium hydroxide once and brine once. The organic solution was concentrated to dryness. The oil was washed with methanol and purified by chromatography to give the title compound.

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated to a minimum and tert-butyl methyl ether
  3. additionwas added
  4. washThe organic layer was washed with dilute acetic acid (4 times) and 0.1N sodium hydroxide once
  5. concentrationThe organic solution was concentrated to dryness
  6. washThe oil was washed with methanol
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-0054602584d94c229415cfa06b3b5270
Source dataset
uspto-grants-2016_01
Patent number
US09243003B2

Reaction notes

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