Piperidine → 10-(2-Benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-(1)benzopyropyrano(6,7-8-I,j)quinolizin-11-one

HRID 376230Notes

Reaction equation

HRID 376230 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH3:16][C:17]1([CH3:35])[C:28]2=[C:29]3[N:20]([CH2:21][CH2:22][C:23](C)([CH3:33])[C:24]3=[C:25](O)[C:26](C=O)=[CH:27]2)[CH2:19][CH2:18]1.N1CCCCC1>C(#N)C>[CH3:16][C:17]1([CH3:35])[C:28]2=[C:29]3[N:20]([CH2:21][CH2:22][C:23]([CH3:24])([CH3:33])[C:15]3=[C:14]3[O:13][C:11](=[O:12])[C:10]([C:2]4[S:1][C:5]5[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:3]=4)=[CH:25][C:26]3=[CH:27]2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 359796Ethyl (1,3-benzothiazol-2-yl)acetateHCID 7370898-Hydroxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde

Product 1

HCID 511280510-(2-Benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-(1)benzopyropyrano(6,7-8-I,j)quinolizin-11-oneYield 80.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 12.28 g of ethyl 2-(benzothiazolyl)acetate was refluxed with 15 g of 1,1,7,7-tetramethyl-8-hydroxy-9-formyljulolidine in 120 mL of acetonitrile containing 2 mL of piperidine as a base catalyst for 15 h. Upon cooling, the precipitated bright orange solid was filtered and washed with some acetonitrile to give 19 g (79% yield) of pure dye C-545T: m.p. 229-230° C.; Tg=100° C.

Workup

  1. temperatureUpon cooling
  2. filtrationthe precipitated bright orange solid was filtered
  3. washwashed with some acetonitrile

Sources & evidence

ORD record
ord-6bd31264e11c438d8fbe3ce87d8d95f3
Source dataset
uspto-grants-2000_02
Patent number
US06020078

Reaction notes

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