Piperidine → HCID 135502653, compound

HRID 1437017Notes

Reaction equation

HRID 1437017 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[C:14](SC)=[N:13][C:12]=2[CH:24]=1>N1C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[C:14]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:13][C:12]=2[CH:24]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 136056013HCID 136056013, compound

Product 1

HCID 135502653HCID 135502653, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
160 °C

Procedure

Piperidine (37 mg, 0.44 mmol) was added to crude 8-chloro-11-methylsulfanyl-5H-dibenzo[b,e][1,4]diazepine (166JO50) (90 mg, purity 50%, 0.218 mmol) in pyridine (2 mL) and the resulting mixture was heated in a capped tube at 160° C. for 10 h. The mixture was concentrated and flash chromatographed (SiO2, heptane:EtOAc 8:1-6:1) to give 12 mg of the title compound (166JO69A). MS (ESI) 312 (MH+). Purity for MH+ (UV/MS) 100/100.

Workup

  1. concentrationThe mixture was concentrated
  2. customflash chromatographed (SiO2, heptane:EtOAc 8:1-6:1)

Sources & evidence

ORD record
ord-ace155f2ff1a447698aebe919188349b
Source dataset
uspto-grants-2009_11
Patent number
US07622461B2

Reaction notes

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