Dichloromethane → HCID 68435133, compound

HRID 1867433Notes

Reaction equation

HRID 1867433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH:22]3[CH2:24][O:23]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH:22]([OH:23])[CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 10796Cesium carbonateHCID 87453574HCID 87453574, compound

Product 1

HCID 68435133HCID 68435133, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 0.30 g (0.81 mmol) of (rac)-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-oxiranylmethyl-[1,4]diazepan-5-one in 0.3 ml of DMA was treated with 0.19 ml (1.22 mmol) of piperidine and 0.265 g (0.81 mmol) of cesium carbonate. The reaction was stirred over night at RT, CH2Cl2 was added, filtrated and evaporated. Crystallization (CH2Cl2/Et2O) gave 0.16 g (43%) of the title compound as pink crystalline solid. MS: 454.2 (MH+, 2Cl).

Workup

  1. filtrationfiltrated
  2. customevaporated
  3. customCrystallization (CH2Cl2/Et2O)

Sources & evidence

ORD record
ord-d23e5b10ef5147fe976f541c1d3dc899
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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