Water → HCID 18607001, compound

HRID 1906412Notes

Reaction equation

HRID 1906412 reaction equation
[OH:1][C@@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:7][C:6]2[C:17]3[C:22]([CH:23]=[CH:24][C:5]=2[NH:4][C:3]1=[O:25])=[CH:21][CH:20]=[CH:19][CH:18]=3.C(=O)([O-])[O-].[K+].[K+].[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36]Cl.O>C(OCC)(=O)C>[OH:1][C@@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:7][C:6]2[C:17]3[C:22]([CH:23]=[CH:24][C:5]=2[N:4]([CH2:36][CH2:35][CH2:34][N:33]([CH3:38])[CH3:32])[C:3]1=[O:25])=[CH:21][CH:20]=[CH:19][CH:18]=3

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamine2×HCID 13823434HCID 13823434, compound

Product 1

HCID 18607001HCID 18607001, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 1.7 g of (±)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one, 0.75 g potassium carbonate and 0.7 g of 3-dimethylaminopropyl chloride in 30 mL of ethyl acetate was stirred and heated at reflux for 2 hours then an additional 0.2 g of 3-dimethylaminopropyl chloride was added four times at 2 hour intervals. The mixture was heated at reflux for a total of 12 hours then to the mixture ethyl acetate and water were added. The organic phase was separated, washed with brine and dried (magnesium sulfate). Removal of the solvent gave 2.1 g (100%) (±)-cis-2,3-dihydro-3-hydroxy-5-[3-(dimethylamino)propyl]-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one. A sample was crystallized from ether, mp 123°-124°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was heated
  4. temperatureat reflux for a total of 12 hours
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried (magnesium sulfate)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-6b6003d36ecf456289ce393e0730dc3d
Source dataset
uspto-grants-1987_03
Patent number
US04652561

Reaction notes

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