Water → HCID 46848690, compound

HRID 929419Notes

Reaction equation

HRID 929419 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:11]([NH:18][C:19]([NH2:21])=[NH:20])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].O>CN(C=O)C>[NH2:21][C:19]1[N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:2]=[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[N:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 30153231-Bromooctan-2-oneHCID 178454308HCID 178454308, compound

Product 1

HCID 46848690HCID 46848690, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-bromooctan-2-one (1.00 g, 4.83 mmol) was placed in a 50 mL round bottomed flask with a stir bar and dissolved in 10 mL of DMF. Boc guanidine (2.31 g, 14.89 mmol) was then added to the reaction mixture and it was allowed to stir for 48 hours. Water was then added to the reaction mixture and it was placed in a separatory funnel. The mixture was then extracted twice with ethyl acetate, washed twice with water, washed twice with brine, concentrated de vacuo and then purified via column chromatography (5% methanol/95% dichloromethane) to provide tert-butyl 2-amino-4-hexyl-1H-imidazole-1-carboxylate as a hygroscopic light yellow solid (0.74 g, 57% yield). 1H NMR (300 MHz, CDCl3) δ 6.69 (s, 2H), δ 6.34 (s, 1H), δ 2.20 (t, J=7.5 Hz, 2H), δ 1.44 (bs, 11H), 1.17 (s, 6H), δ 0.76 (s, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 151.1, 149.6, 139.3, 105.7, 84.1, 31.8, 29.2, 28.4, 28.3, 28.0, 22.7, 14.2 ppm; IR νmax (cm−1) 3421, 2109, 1644, 1442, 1204, 1142; HRMS (ESI) calcd for C14H25N3O2 (M+) 267.1946, found 267.1940. Then, tert-butyl 2-amino-4-hexyl-1H-imidazole-1-carboxylate was dissolved in a 1:4 mixture of trifluoroacetic acid/dichloromethane and allowed to stir for five hours and then concentrated de vacuo. The sample was then dissolved with a dilute HCl/methanol (5 drops HCl/50 mL of methanol) and then concentrated in vacuo to provide 4-(5phenylpentyl)-1H)-imidazol-2-amine hydrochloride as a hygroscopic light yellow solid (0.57 g, 57% overall yield). 1H NMR (300 MHz, CD3OD) δ 6.34 (bs, 3H), δ 2.41 (t, J=7.5 Hz, 2H), δ1.56 (m, 2H), δ 1.28 (bs, 6H), δ 0.82 (t, J=6.6 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 151.4, 131.9, 111.9, 35.3, 32.4, 31.9, 28.3, 26.3, 17.1 ppm; IR νmax (cm−1) 3411, 2099, 1638; HRMS (ESI) calcd for C9H17N3 (M+) 167.1422, found 167.1416.

Workup

  1. customwas placed in a separatory funnel
  2. extractionThe mixture was then extracted twice with ethyl acetate
  3. washwashed twice with water
  4. washwashed twice with brine
  5. concentrationconcentrated de vacuo
  6. custompurified via column chromatography (5% methanol/95% dichloromethane)

Sources & evidence

ORD record
ord-f9207ad3af73480ebe7fa473cfd5beec
Source dataset
uspto-grants-2016_03
Patent number
US09295257B2

Reaction notes

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