Dichloromethane → HCID 70366955, compound

HRID 1651516Notes

Reaction equation

HRID 1651516 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[CH2:15][CH2:16][N:8]([C:9]=23)[C:7]2[CH:17]=[CH:18]C=[CH:20][C:6]=2[NH:5]1.[C:21]([O:28]CC)(=O)[C:22]([O:24]CC)=O.Cl[CH2:32]Cl>>[CH3:18][C:17]1[C:22](=[O:24])[C:21](=[O:28])[CH:20]=[C:6]2[N:5]3[CH:32]=[CH:1][N:2]=[CH:3][C:4]3=[C:10]3[CH2:11][CH2:12][CH2:13][C:14]4[CH:15]=[CH:16][N:8]([C:9]=43)[C:7]=12

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7268Diethyl OxalateHCID 14156741HCID 14156741, compound

Product 1

HCID 70366955HCID 70366955, compoundYield 46.7%

Conditions

Temperature
140 °C

Procedure

N-methyl-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-methanamine (2.5 g), and diethyl oxalate (1.6 g), were combined and heated to 140° C. over a period of 45 min, then to 180° C. over 15 min. The reaction mixture was maintained at this temperature for 1 hr. The reaction mixture was cooled, dissolved in a small volume of dichloromethane, placed on a column of silica gel and eluted with 2.5% methanol-dichloromethane to yield 1.4 g, (46.7%) of product.

Workup

  1. temperatureThe reaction mixture was maintained at this temperature for 1 hr
  2. temperatureThe reaction mixture was cooled
  3. washeluted with 2.5% methanol-dichloromethane

Sources & evidence

ORD record
ord-7cafbc59a9204e229071fd1832913925
Source dataset
uspto-grants-1990_05
Patent number
US04929615

Reaction notes

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