Diazald → HCID 178519875, compound

HRID 1682768Notes

Reaction equation

HRID 1682768 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]([OH:34])([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)[C:10](=[O:19])[C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:35](=[CH2:37])=[N-:36].CN(N=O)S(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][C:25]([OH:34])([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:26][CH2:27]2)[C:10]([C:11]2[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[N:36][NH:35][CH:37]=2)=[O:19])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6628DiazaldHCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 18930289HCID 18930289, compound

Product 1

HCID 178519875HCID 178519875, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-(3,4-dichlorophenyl)-6-(4-hydroxy-4-phenylpiperidino)-1-phenyl-hex-1-yne-3-one (0.30 g) in diethyI ether (25 mL) was cooled to 0° C. and was treated with diazomethane (generated by the reaction of and ethereal solution of N-methyl-N-nitroso-p-toluenesulfonamide with ethanolic potassium hydroxide (Anal. Chem., 45, 2302, 1973)). The resulting mixture was allowed to warm to room temperature and stirred for 3 days. The solvent was evaporated. Radial chromatography, eluting with dichloromethane:methanol (gradient 97.5:2.5, 95:5), afforded the title compound (50 mg) as a white powder; mp 112°-114° C.; NMR: 8.13 (s,1), 7.56-7.26 (m,12), 7.08 (d,1), 4.33 (broad s,1), 2.68 (m,2), 2.37 (m,3), 2.05 (broad s,1), 1.86 (broad s,1), 1.73-1.43 (m,5); MS: m/z=534(M+l). Analysis for C30H29Cl2N3O2 ·0.75 H2O: Calculated: C, 65.75; H, 5.61; N, 7.67; Found: C, 65.71; H, 5.60; N, 7.83.

Workup

  1. customThe solvent was evaporated
  2. washRadial chromatography, eluting with dichloromethane

Sources & evidence

ORD record
ord-8da9ff4d5b3a455a9c369c03bf3c3a9e
Source dataset
uspto-grants-1997_06
Patent number
US05635509

Reaction notes

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