Water → HCID 66931489, compound

HRID 593341Notes

Reaction equation

HRID 593341 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[CH2:13][O:12][CH2:11][C:10]([NH2:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](Cl)([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1.O>ClCCl>[CH3:45][O:44][C:41]1[CH:40]=[CH:39][C:38]([C:31]([NH:14][C:10]2[CH2:11][O:12][CH2:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)([CH3:15])[N:9]=2)([C:28]2[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 58155185HCID 58155185, compound

Product 1

HCID 66931489HCID 66931489, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (RS)-5-(3-bromo-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine (3.7 g, 13.8 mmol) and triethylamine (1.5 g, 1.1 eq) in dichloromethane (20 ml) was cooled to 0° C. and 4,4′-dimethoxytriphenylmethyl chloride (5.12 g, 1.1 eq) was added. The reaction mixture was stirred at room temperature overnight. Thereafter, water was added to the mixture and the organic phase was separated, dried over sodium sulphate and concentrated at reduced pressure. The crude was purified by chromatography on silica gel to yield the (RS)-[bis-(4-methoxy-phenyl)-phenyl-methyl]-[5-(3-bromo-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-amine as a yellow oil (7.0 g, 99%). Mass (calculated) C3H31BrN2O3 [571.52]; (found) [M+H]+=571.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated at reduced pressure
  4. customThe crude was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7f7d45fc8d034672939c5c7f0711b4c1
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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