Benzene → HCID 71621990, compound

HRID 2099020Notes

Reaction equation

HRID 2099020 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:7]1[CH2:12][CH2:11]C[CH2:9][CH2:8]1.[CH3:13][O:14][C:15](=[O:26])[CH2:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.C(#[N:29])C>>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[C:16]1[C:15](=[O:26])[O:14][C:13]2[C:3]([CH:2]=1)=[CH:4][CH:5]=[C:6]([N:7]1[CH2:8][CH2:9][NH:29][CH2:11][CH2:12]1)[CH:1]=2

Participants

5

Reactant 4

HCID 241BenzeneHCID 6342AcetonitrileHCID 8082PiperidineHCID 358756Methyl (1,3-benzothiazol-2-yl)acetate

Product 1

HCID 71621990HCID 71621990, compound

Procedure

890 mg (5 mmol) 3-Piperazin-1-yl-phenol are suspended in 100 mL EtOH and treated with 0.42 mL (1 eq.) 12N HCl at a temperature below 10° C. The suspension is stirred an hour and slowly evaporated. The remaining beige powder is dried under high vacuum, then taken up in 60 mL DMF. The solution is cooled to 5° C. under argon, 0.503 mL (1.1 eq.) POCl3 added dropwise and the reaction mixture stirred for an hour at room temperature, then 30 minutes at 80° C., and finally allowed to cool to room temperature, upon which 2 g (3 eq.) solid potassium carbonate is added. The suspension is stirred 30 minutes at room temperature then evaporated, and the residue resuspended and stirred in a 1:1 mixture of dichloromethane and isopropanol. The suspension is filtered, the filtrate evaporated and dried to yield 600 mg crude 2-hydroxy4-piperazin-1-yl-benzaldehyde. This material is taken up in 40 mL of a 1:1 mixture of benzene and acetonitrile, 2.5 mL (5 eq.) piperidine and 683 mg (0.66 eq.) benzothiazol-2-yl-acetic acid methyl ester are added under argon and the reaction mixture refluxed for an hour. The product is extracted with dichloromethane and brine at 0° C., the combined organic phases dried with sodium sulphate, filtered and evaporated, then triturated with diisopropylether to yield 800 mg desired product (crude).

Workup

  1. additionare added under argon
  2. temperaturethe reaction mixture refluxed for an hour
  3. extractionThe product is extracted with dichloromethane and brine at 0° C.
  4. dry with materialthe combined organic phases dried with sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customtriturated with diisopropylether

Sources & evidence

ORD record
ord-c4981a81a6b945d2bfe06ae6eced20f6
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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