Sodium Carbonate → HCID 67779906, compound

HRID 129550Notes

Reaction equation

HRID 129550 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:6][NH:7][C@H:8]([CH3:20])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:33](Br)[C:34]([OH:36])=[O:35])[CH:30]=[CH:31][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O>[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:6][N:7]([C@H:8]([CH3:20])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[CH:33]([C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([Cl:26])[CH:28]=1)[C:34]([OH:36])=[O:35]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 22626651HCID 22626651, compoundHCID 54069661(R)-N-(3,4-dimethoxybenzyl)-1-(3,4-dimethoxyphenyl)-prop-2-ylamine

Product 1

HCID 67779906HCID 67779906, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5.3 g. of (R)-N-(3,4-dimethoxybenzyl)-1-(3,4-dimethoxyphenyl)-prop-2-ylamine, 3.94 g. of 3-chlorophenylcarboxymethyl bromide, and 4.9 g. of sodium carbonate in 50 mL of methylene chloride and 20 mL of water is stirred at room temperature for 16 hours. Upon completion of the reaction as determined by TLC and HPLC, the reaction mixture is diluted with methylene chloride, the aqueous layer is separated, and the organic layer is washed twice with 10% aqueous hydrochloric acid, dried over magnesium sulfate, and concentrated to yield (R)-N-(3,4-dimethoxybenzyl)-N-(3-chlorophenylcarboxymethyl)-1-(3,4-dimethoxyphenyl)-prop-2-ylamine hydrochloride.

Workup

  1. additionA mixture of 5.3 g
  2. customUpon completion of the reaction
  3. customthe aqueous layer is separated
  4. washthe organic layer is washed twice with 10% aqueous hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9275af94adaa4f8d8df0583769ccf7d6
Source dataset
uspto-grants-1995_11
Patent number
US05468865

Reaction notes

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