Dichloromethane → HCID 89923787, compound

HRID 1752649Notes

Reaction equation

HRID 1752649 reaction equation
Cl.Cl.[O:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:5][CH2:4]1.C([O-])(O)=O.[Na+].[N:20]#[C:21]Br.C(Cl)Cl>C(O)C>[O:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][N:12]([C:21]#[N:20])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 441204811-(Oxan-4-yl)piperazine--hydrogen chloride (1/2)

Product 1

HCID 89923787HCID 89923787, compoundYield 131.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1-(tetrahydro-2H-pyran-4-yl)piperazine dihydrochloride (600 mg, 2.467 mmol) in anhydrous Ethanol (10 mL) was added solid NaHCO3 (1555 mg, 18.51 mmol) followed by cyanic bromide (523 mg, 4.93 mmol) and the mixture was stirred at ambient temperature. The mixture was diluted by 50 mL of CH2Cl2 and the solids were filtered off. The filtrated was concentrated in vacuo to afford to give the title compound (632 mg, 3.24 mmol, >100% yield). 1H NMR (400 MHz, Chloroform-d) δ ppm=4.02 (dd, J=3.8, 11.2 Hz, 2H), 3.42-3.31 (m, 2H), 3.31-3.22 (m, 4H), 2.74-2.61 (m, 4H), 2.59-2.47 (m, 1H), 1.73 (d, J=11.5 Hz, 2H), 1.67-1.49 (m, 2H); LC/MS (m/z) ES+ (ELSD)=196.1 (M+1).

Workup

  1. filtrationthe solids were filtered off
  2. concentrationThe filtrated was concentrated in vacuo
  3. customto afford

Sources & evidence

ORD record
ord-eadd94c3f917482a9919dc2f9f0c1ac9
Source dataset
uspto-grants-2015_10
Patent number
US09163023B2

Reaction notes

Loading…