1,5-Dibromopentane → HCID 16108954, compound

HRID 1444715Notes

Reaction equation

HRID 1444715 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 3354775tert-butyl N-{[4-(aminomethyl)phenyl]methyl}carbamate

Product 1

HCID 16108954HCID 16108954, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of (4-aminomethyl-benzyl)-carbamic acid tert-butyl ester (4.06 g, 17.2 mmol), 1,5-dibromo-pentane (2.60 mL, 19.1 mmol) and potassium carbonate (8.96 g, 65.1 mmol) in acetonitrile (160 mL) was refluxed overnight under N2. The reaction was cooled to r.t. and filtered. The filtrate was concentrated in vacuo and chomatographed on silica (CH2Cl2→CH2Cl2/MeOH with 2N NH3=25/1) to yield the desired product.

Workup

  1. temperaturewas refluxed overnight under N2
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4cc1424b43544ff2bd9bac32fa1a44cc
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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