2-Chloro-N,N-dimethylethylamine → HCID 15611327, compound

HRID 845022Notes

Reaction equation

HRID 845022 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:16](=[O:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[NH:13][C:12](=[O:22])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:25][N:26]([CH2:28][CH2:29]Cl)[CH3:27]>C1(C)C=CC=CC=1>[CH3:25][N:26]([CH3:27])[CH2:28][CH2:29][N:13]1[C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16](=[O:17])[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11][C:12]1=[O:22]

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamine2×HCID 24758Sodium hydrideHCID 15611326HCID 15611326, compound

Product 1

HCID 15611327HCID 15611327, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To azeotropically dried 4,5-Dihydro-5-(4-methoxyphenyl)-1-benzazocine-2,6(1H,3H)-dione (1.80 g) in toluene (40 ml) was added 60% sodium hydride in mineral oil (0.27 g) and the mixture stirred under nitrogen at room temperature overnight. The slurry was stirred and heated to 70° for 15 minutes, and the freshly prepared N,N-dimethylaminoethyl chloride (1.25 g) was slowly added. After a half an hour at 70°, a further 1.25 g of N,N-dimethylaminoethyl chloride was added. The temperature was then raised to 90° and maintained for 3 hours. The cooled reaction mixture was filtered through sintered glass and the filtered solid discarded. The filtrate was evaporated and the residue was triturated with ether. The resulting white solid was collected on a filter; wt. 1.58 g (72%), mp=115-116. Recrystallization from ether gave pure titled product; wt. 1.25 g, mp=116°-117°.

Workup

  1. stirringThe slurry was stirred
  2. temperatureheated to 70° for 15 minutes
  3. waitAfter a half an hour at 70°
  4. temperatureThe temperature was then raised to 90°
  5. temperaturemaintained for 3 hours
  6. customThe cooled reaction mixture
  7. filtrationwas filtered through sintered glass
  8. customThe filtrate was evaporated
  9. customthe residue was triturated with ether
  10. customThe resulting white solid was collected on a filter
  11. customRecrystallization from ether

Sources & evidence

ORD record
ord-5538d25dc9b04264b7f851175a174afd
Source dataset
uspto-grants-1988_07
Patent number
US04755505

Reaction notes

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