Hydrochloric Acid → HCID 46850703, compound

HRID 929418Notes

Reaction equation

HRID 929418 reaction equation
[N+:1]([CH:4]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:5](=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O.Cl.[N:24]#[C:25][NH2:26]>[Pd]>[CH2:18]([C:4]1[NH:1][C:25]([NH2:26])=[N:24][C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 468485157-Nitro-1-phenyldodecan-6-one

Product 1

HCID 46850703HCID 46850703, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

7-Nitro-1-phenyldodecan-6-one (0.090 g, 0.29 mmol) reacted with concentrated HCl (1.45 mmol) and palladium, 5 wt. % on activated carbon (0.125 g, 0.060 mmol) under H2, then reacted with cyanamide (0.062 g, 1.47 mmol) according to the general procedure. Purification by column chromatography gave 0.071 g (81%) over two steps as a yellow oil: 1H NMR (300 MHz, CD3OD) δ 7.20 (m, 2H), 7.14 (m, 3H), 2.59 (t, J=7.5 Hz, 2H), 2.42 (m, 4H), 1.56 (m, 6H), 1.32 (m, 6H), 0.90 (t, J=7.2 Hz, 3H) ppm; 13C NMR (75 MHz, CD3OD) δ 146.3, 142.5, 128.3, 128.1, 125.6, 122.1, 121.8, 35.5, 31.1, 31.1, 28.7, 28.7, 28.2, 23.1, 23.0, 22.3, 13.3 ppm; IR νmax (cm−1) 3169, 2928, 2857, 1680, 1453, 1202, 1030, 746, 699; HRMS (FAB) calcd for C19H29N3 (MH+) 300.2434, found 300.2441.

Workup

  1. customPurification by column chromatography
  2. customgave 0.071 g (81%) over two steps as a yellow oil

Sources & evidence

ORD record
ord-0f59a4483c774bc895968419dde2bd11
Source dataset
uspto-grants-2016_03
Patent number
US09295257B2

Reaction notes

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