Hydrochloric Acid → 4-(5-phenylpentyl)-5-propyl-1H-imidazol-2-amine

HRID 929416Notes

Reaction equation

HRID 929416 reaction equation
[N+:1]([CH:4]([C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][CH2:6][CH3:7])([O-])=O.Cl.[N:22]#[C:23][NH2:24]>[Pd]>[C:14]1([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[N:22]=[C:23]([NH2:24])[NH:1][C:4]=2[CH2:5][CH2:6][CH3:7])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 468483514-Nitro-10-phenyldecan-5-one

Product 1

HCID 468507014-(5-phenylpentyl)-5-propyl-1H-imidazol-2-amine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-Nitro-10-phenyldecan-5-one (0.084 g, 0.30 mmol) reacted with concentrated HCl (1.50 mmol) and palladium, 5 wt. % on activated carbon (0.129 g, 0.060 mmol) under H2, then reacted with cyanamide (0.064 g, 1.50 mmol) according to the general procedure. Purification by column chromatography gave 0.025 g (30%) over two steps as a yellow oil: 1H NMR (300 MHz, CD3OD) δ 7.20 (m, 2H), 7.15 (m, 3H), 2.60 (t, J=7.2 Hz, 2H), 2.40 (m, 4H), 1.56 (m, 6H), 1.30 (m, 2H), 0.92 (t, J=7.2 Hz, 3H) ppm; 13C NMR (100 MHz, CD3OD) δ 146.4, 142.5, 128.3, 128.1, 125.6, 122.1, 121.9, 35.5, 31.1, 28.8, 28.2, 25.0, 23.0, 22.3, 12.6 ppm; IR νmax (cm−1) 3165, 2931, 1680, 1453, 1031, 747, 699; HRMS (FAB) calcd for C17H25N3 (MH+) 272.2121, found 272.2127.

Workup

  1. customPurification by column chromatography
  2. customgave 0.025 g (30%) over two steps as a yellow oil

Sources & evidence

ORD record
ord-6ca90f5e5fd348489caaba634035420c
Source dataset
uspto-grants-2016_03
Patent number
US09295257B2

Reaction notes

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