Benzyl Chloride → HCID 11713432, compound

HRID 1173365Notes

Reaction equation

HRID 1173365 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][O:16][C:17]([C:19]1[CH:20]=[C:21]([CH3:43])[C:22]2[O:28][C:27]3[C:29]([Cl:39])=[CH:30][C:31]([N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)=[CH:32][C:26]=3[CH2:25][S:24](=[O:41])(=[O:40])[C:23]=2[CH:42]=1)=[O:18]>CN(C=O)C>[CH3:15][O:16][C:17]([C:19]1[CH:20]=[C:21]([CH3:43])[C:22]2[O:28][C:27]3[C:29]([Cl:39])=[CH:30][C:31]([N:33]4[CH2:34][CH2:35][N:36]([CH2:7][C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[CH2:37][CH2:38]4)=[CH:32][C:26]=3[CH2:25][S:24](=[O:40])(=[O:41])[C:23]=2[CH:42]=1)=[O:18]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

Product 1

HCID 11713432HCID 11713432, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of cesium carbonate (0.33 g, 0.82 mmol) and benzyl chloride (0.1 mL, 0.82 mmol) was added to a solution of 4-chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester (free base of example 16, 0.3 g, 0.68 mmol) in DMF (10 mL) and heated at 80° C. for 5 h. Reaction mixture was concentrated, water (10 mL) was added and the solid filtered. The crude obtained was purified by column chromatography (silica gel, 1% to 3% methanol in chloroform) to obtain the title compound. Yield: 0.11 g, (30.4%); 1H NMR (DMSO-d6, 300 MHz): δ 2.62 (s, 3H, CH3), 3.18 (s, 4H, 2CH2), 3.31 (s, 4H, 2CH2), 3.50 (s, 2H, CH2), 3.85 (s, 3H, OCH3), 5.14 (s, 2H, CH2), 7.04 (s, 1H, Ar), 7.11 (s, 1H, Ar), 7.3-7.32 (m, 5H, Ar), 8.08 (s, 1H, Ar), 8.14 (s, 1H, Ar); MS: m/e (ES+) 528 (M+1); analysis: C27H27ClN2O5S requires C, 61.53; H, 5.16; N, 5.32; Cl, 6.73; S, 6.08. found: C, 61.22; H, 4.99; N, 4.82; Cl, 6.91; S, 6.15%.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. additionwater (10 mL) was added
  4. filtrationthe solid filtered
  5. customThe crude obtained
  6. customwas purified by column chromatography (silica gel, 1% to 3% methanol in chloroform)

Sources & evidence

ORD record
ord-87bb9742b4094c4ca4adf74e3ab25fe4
Source dataset
uspto-grants-2010_11
Patent number
US07834052B2

Reaction notes

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