Cyanogen Bromide → HCID 23294469, compound

HRID 1955231Notes

Reaction equation

HRID 1955231 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH2:24])[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:25]#[C:26]Br>CO.C(#N)C>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]3=[N:23][C:26](=[NH:25])[N:24]=[C:19]3[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 23294226HCID 23294226, compound

Product 1

HCID 23294469HCID 23294469, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-benzyl-1-[(3,4-diaminophenoxy)ethyl]piperidine (202 mg, 0.62 mmol) in MeOH (1.5 mL) was added 130 μL of 5.0 M solution of cyanogen bromide in acetonitrile. The resulting mixture was stirred at r.t. under N2 for 24 h, then evaporated, and the residue was purified by chromatography over silica gel (CHCl3 --MeOH, 4:1) to give 174 mg (80%) of the title compound as a viscous oil. 1H NMR (CDCl3): 1.35-1.46 (m, 2H), 1.50-1.67 (m, 3H), 2.04-2.12 (m, 2H), 2.539 (d, 2H, J=7), 2.773 (t, 2H, J=6), 3.00-3.03 (m, 2H), 3.50 (bs, 1H), 4.035 (t, 2H, J=6), 6.243 (dd, 1H, J=8; 3), 6.317 (d, 1H, J=3), 6.614 (d, 1H, J=8), 7.12-7.30 (m, 5H).

Workup

  1. customevaporated
  2. customthe residue was purified by chromatography over silica gel (CHCl3 --MeOH, 4:1)

Sources & evidence

ORD record
ord-ad902e95746e46d0bcce650dbc76253e
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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