Hydrochloric Acid → HCID 18972562, compound

HRID 2395117Notes

Reaction equation

HRID 2395117 reaction equation
C([Li])(C)(C)C.[CH2:6]([N:12]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].CN(CCN(C)C)C.[CH:34](N1CCCCC1)=[O:35].Cl>C(OCC)(=O)C.C(OCC)C>[CH2:6]([N:12]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:34]=[O:35])[C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 174291-PiperidinecarboxaldehydeHCID 1897263110-Hexyl-10H-phenothiazineHCID 178418306HCID 178418306, compound

Product 1

HCID 18972562HCID 18972562, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

38.6 ml of tert-butyllithium solution (1.4M in hexane) were slowly added dropwise at -78° under argon and while stirring to a solution of 11.80 g (41.6 mmol) of 10-hexyl-phenothiazine in 125 ml of abs. diethyl ether and 12.5 ml of N,N,N,N-tetramethylethylenediamine. The reaction mixture was stirred at -75° for 16 hours, brought slowly to 0°, treated with 6.92 ml (1.5 eq.) of N-formylpiperidine, stirred at 0° for 1 hour and then poured into ice, 100 ml of 0.1N hydrochloric acid solution and 250 ml of ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was chromatographed on 1 kg of silica gel with ethyl acetate/hexane (1:1), whereupon 6.33 g (48.8%) of 10-hexyl-phenothiazine-4-carbaldehyde were obtained as a light yellowish oil. IR (film): 3064w, 2927m, 2854m, 2731w, 1689s, 1561m, 1455s, 1388w, 1336m, 1286m, 1259s, 1052w, 784m, 750m, 724m.

Workup

  1. custombrought slowly to 0°
  2. stirringstirred at 0° for 1 hour
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on 1 kg of silica gel with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-fef89c08270f4e6980f4b6543134a1dc
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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