Water → HCID 66931489, compound

HRID 1929480Notes

Reaction equation

HRID 1929480 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, compound

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 sulfate 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% of theory). Mass (calculated) C3H31BrN2O3 [571.52]; (found) [M+H]+=571.

Workup

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

Sources & evidence

ORD record
ord-d09ab4578c654d1c98f4bf8daee90a20
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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