Hydrochloric Acid → HCID 136364245, compound

HRID 428327Notes

Reaction equation

[N:1]([O-])=O.[Na+].Cl.[CH3:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.[CH:14]([N:17]([CH:34]([CH3:36])[CH3:35])[CH2:18][CH2:19][C@@H:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:16])[CH3:15].[OH-].[Na+]>C1COCC1.O>[CH:34]([N:17]([CH:14]([CH3:16])[CH3:15])[CH2:18][CH2:19][C@@H:20]([C:27]1[CH:32]=[C:31]([N:1]=[N:11][C:10]2[CH:12]=[CH:13][C:7]([CH3:6])=[CH:8][CH:9]=2)[CH:30]=[CH:29][C:28]=1[OH:33])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

NaNO2 (0.27 g, 4.30 mmol) was added to a mixture of hydrochloric acid (0.64 mL, 7.70 mmol, conc.) and p-methylaniline (0.41 g, 3.80 mmol) in ice-water (20 mL). The mixture was stirred at 0° C. for 10 min. and then added to an ice-cold solution of (R)-N,N-diisopropyl-3-(2-hydroxyphenyl)-3-phenylpropanamine (1.00 g, 3.21 mmol) in THF (3 mL), H2O (12 mL) and sodium hydroxide (0.69 g, 17.32 mmol). After stirring the mixture for 20 minutes, it was extracted with toluene, dried (MgSO4), and evaporated to give an oil, which was chromatographed on (toluene-ethyl acetate-triethylamine 8:1:1) to give 0.83 g, 1.93 mmol, (60%) of the title compound. 1H NMR (CDCl3) δ1.12 (d, 6H), 1.19 (d, 6H), 2.22 (m, 1H), 2.43 (m, 5H), 2.79 (m, 1H), 3.32 (m, 2H), 4.57 (d, 1H), 6.98 (d, 1H), 7.24 (m, 3H), 7.36 (m, 4H), 7.66 (m, 4H).

Workup

stirringAfter stirring the mixture for 20 minutes
extractionit was extracted with toluene
dry with materialdried (MgSO4)
customevaporated
customto give an oil, which
customwas chromatographed on (toluene-ethyl acetate-triethylamine 8:1:1)

Sources & evidence

ORD record: ord-f9af7e29c0164efebf53663b0cbe53b5
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313132B1

Reaction notes

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