Tributylphosphine → HCID 69637133, compound

HRID 1825733Notes

Reaction equation

HRID 1825733 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2/[CH:11]=[C:12]1\[S:13][C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[NH:16][C:17]\1=[O:18].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.O[CH2:55][CH2:56][N:57]1[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1>O1CCCC1>[N:57]1([CH2:56][CH2:55][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3/[CH:11]=[C:12]2\[S:13][C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[NH:16][C:17]\2=[O:18])[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 18232N-PiperidinoethanolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 69637194HCID 69637194, compound

Product 1

HCID 69637133HCID 69637133, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-2[(5-hydroxyindol-3-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one (1.00 g, 3.24 mmol) and 1,1′-(azodicarbonyl)dipiperidine (1.23 g, 4.87 mmol) in dry tetrahydrofurane-(40 ml), tributylphosphine (0.98 g, 4.87 mmol) was added under nitrogen atmosphere keeping the mixture at 0–5° C. After 5 min N-(2-hydroxyethyl)piperidine (0.63 g, 4.88 mmol) was added at the same temperature. The cooling bath was removed and the mixture stirred at room temperature for 48 h. Then the solvent was removed under reduced pressure and the residue chromatographed (silica gel, eluent, ethyl acetate:ethanol (90:10) to (80:20)) to yield 0.2 g (22%) of the entitled product.

Workup

  1. customat 0–5° C
  2. customThe cooling bath was removed
  3. customThen the solvent was removed under reduced pressure
  4. customthe residue chromatographed (silica gel, eluent, ethyl acetate:ethanol (90:10) to (80:20))

Sources & evidence

ORD record
ord-4205e778472943009f0afe7f3c717565
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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