Hydroxide → HCID 21153174, compound

HRID 1447654Notes

Reaction equation

HRID 1447654 reaction equation
[OH-].[CH3:2][N:3]([CH3:16])[C@@H:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[C@H:6]([OH:15])[CH2:5]1.Cl[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25]>CS(C)=O>[CH3:2][N:3]([CH3:16])[C@@H:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[C@H:6]([O:15][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])[CH2:5]1

Participants

5

Reactant 3

HCID 961HydroxideHCID 69451-Chloro-2-nitrobenzeneHCID 86736721HCID 86736721, compound

Product 1

HCID 21153174HCID 21153174, compoundYield 196.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 11 ml of dimethylsulfoxide and 1.1 g of hydroxide as a 50% oil dispersion was heated in a bath at 70° C. for 30 minutes and after cooling the mixture to 20° C., 4.1 g of cis 7-dimethylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol were added thereto. The mixture was stirred for 10 minutes at room temperature and then 6.32 g of o-chloronitrobenzene were added thereto while cooling in an ice bath. The mixture was stirred for 30 minutes at 20° C. and was extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulfate and was filtered. The filtrate was evaporated to dryness under reduced pressure to obtain 12.8 g of cis N,N-dimethyl-5-[2-nitrophenoxy]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-amine in the form of a brown oil.

Workup

  1. temperatureafter cooling the mixture to 20° C.
  2. temperaturewhile cooling in an ice bath
  3. stirringThe mixture was stirred for 30 minutes at 20° C.
  4. extractionwas extracted with methylene chloride
  5. washThe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationwas filtered
  8. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4a3d40def30040e79fb3dceddd1701f7
Source dataset
uspto-grants-1979_12
Patent number
US04177292

Reaction notes

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