Formaldehyde → HCID 69545914, compound

HRID 2086317Notes

Reaction equation

HRID 2086317 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][C:19](=[O:21])[N:18]([NH:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=4)[CH2:25][CH2:24]3)[CH:17]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[OH-].[Na+].[CH2:43]=O>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][C:19](=[O:21])[N:18]([N:22]([CH3:43])[CH:23]3[CH2:24][CH2:25][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=4)[CH2:27][CH2:28]3)[CH:17]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 69545679HCID 69545679, compound

Product 1

HCID 69545914HCID 69545914, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-1-[[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazineacetate (0.30 g) obtained in Example 138 was dissolved in a 37% aqueous solution of formaldehyde (6.5 ml) and formic acid (3.0 ml) and refluxed for 15 hours. The reaction mixture was cooled, made alkaline by adding a 1N aqueous solution of sodium hydroxide, extracted with dichloromethane, dried and concentrated. The residue thus obtained was crystallized from ethanol to obtain the title compound (95 mg) as colorless crystals.

Workup

  1. temperaturerefluxed for 15 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-1153aeab8f934200bf37cd36ab79d7ad
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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