Formaldehyde → Ro4368554

HRID 1005662Notes

Reaction equation

HRID 1005662 reaction equation
Cl.[C:2]1([S:8]([C:11]2[C:19]3[C:14](=[C:15]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]=O>C(O)C.[Pd]>[C:2]1([S:8]([C:11]2[C:19]3[C:14](=[C:15]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)[CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 69351600HCID 69351600, compound

Product 1

HCID 6918682Ro4368554

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-benzenesulfonyl-7-piperazin-1-yl-1H-indole (101) (500 mg, 1.46 mmol) and 1 mL of 37% aqueous formaldehyde in 25 mL of ethanol was hydrogenated at atmospheric pressure in the presence of 250 mg of 10% Pd-C for 30 min. The mixture was filtered, diluted with water and extracted with ethyl acetate. The ethyl acetate was washed with water and brine, dried, and evaporated to yield the crude free base of 3-benzenesulfonyl-7-(4-methyl-piperazin-1-yl)-1H-indole. The hydrochloride salt was crystallized from ethanol-ether to afford 290 mg of (501), m.p. 160-162° C.

Workup

  1. filtrationThe mixture was filtered
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate was washed with water and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-3a751f096c5a485a935238028a02882b
Source dataset
uspto-grants-2004_09
Patent number
US06787535B2

Reaction notes

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