2-Chloro-N,N-dimethylethylamine → HCID 18606597, compound

HRID 235683Notes

Reaction equation

HRID 235683 reaction equation
[OH:1][C@@H:2]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[S:8][C:7]2=[CH:18][CH:19]=[CH:20][C:21]3=[CH:22][CH:23]=[CH:24][C:5](=[C:6]23)[NH:4][C:3]1=[O:25].C(=O)([O-])[O-].[K+].[K+].[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35]Cl>C(OCC)(=O)C>[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][N:4]1[C:3](=[O:25])[C@H:2]([OH:1])[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[S:8][C:7]2=[CH:18][CH:19]=[CH:20][C:21]3=[CH:22][CH:23]=[CH:24][C:5]1=[C:6]23

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamine2×HCID 11430Potassium CarbonateHCID 18606598HCID 18606598, compound

Product 1

HCID 18606597HCID 18606597, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.1 g of (±)-cis-2,3-dihydro-3-hydroxy2-(4-methoxyphenyl)naphtho[1,8-bc]-1,5-thiazocin-4(5H)-one, 0.48 g of powdered potassium carbonate and 0.425 g of 2-dimethylaminoethyl chloride in 25 mL of ethyl acetate was stirred and heated at reflux for 3 hours, then twice an additional 0.10 g of 2-dimethylaminoethyl chloride was added at 3 hour intervals. The mixture was heated at reflux for a total of 17 hours then was cooled to room temperature and filtered. The filtrate was diluted with 40 mL of ethyl acetate and washed with brine (40 mL) and dried (magnesium sulfate). Removal of the solvent gave 1.2 g (92%) of (±)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,8-bc]-1,5-thiazocin-4(5H)- one. A sample of this compound was crystallized from ethyl acetate, mp. 121°-122°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was heated
  4. temperatureat reflux for a total of 17 hours
  5. filtrationfiltered
  6. additionThe filtrate was diluted with 40 mL of ethyl acetate
  7. washwashed with brine (40 mL)
  8. dry with materialdried (magnesium sulfate)
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-06ae52b35c6e40c183a182e598282369
Source dataset
uspto-grants-1987_02
Patent number
US04640930

Reaction notes

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