Hydrochloric Acid → HCID 178437831, compound

HRID 929415Notes

Reaction equation

HRID 929415 reaction equation
[N+:1]([CH:4]([C:7](=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][CH3:6])([O-])=O.Cl.[N:21]#[C:22][NH2:23]>[Pd]>[CH2:5]([C:4]1[NH:1][C:22]([NH2:23])=[N:21][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 46848350HCID 46848350, compound

Product 1

HCID 178437831HCID 178437831, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-Nitro-9-phenylnonan-4-one (0.050 g, 0.19 mmol) reacted with concentrated HCl (0.95 mmol) and palladium, 5 wt. % on activated carbon (0.081 g, 0.038 mmol) under H2, then reacted with cyanamide (0.040 g, 0.95 mmol) according to the general procedure. Purification by column chromatography gave 0.014 g (29%) over two steps as a yellow oil: 1H NMR (300 MHz, CD3OD) δ 7.25 (m, 2H), 7.14 (m, 3H), 2.59 (t, J=7.5 Hz, 2H), 2.42 (m, 4H), 1.63 (m, 4H), 1.28 (m, 2H), 1.13 (t, J=7.5 Hz, 3H) ppm; 13C NMR (75 MHz, CD3OD) δ 146.2, 142.4, 128.2, 128.1, 125.5, 123.6, 121.3, 35.5, 31.1, 28.7, 28.1, 22.9, 16.5, 13.1 ppm; IR νmax (cm−1) 3327, 2934, 1680, 1453, 1016, 749; HRMS (FAB) calcd for C16H23N3 (MH+) 258.1965, found 258.1973.

Workup

  1. customPurification by column chromatography
  2. customgave 0.014 g (29%) over two steps as a yellow oil

Sources & evidence

ORD record
ord-0fa285ea9d914d6a9aeb92a6c73ba178
Source dataset
uspto-grants-2016_03
Patent number
US09295257B2

Reaction notes

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