Hydrochloric Acid → 4-((3-(5-Methyl-1H-tetrazol-1-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine

HRID 391470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391470
[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=2)[CH2:10][O:11][CH2:12][C:13]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[N:5]=[N:4][N:3]=1.Cl>C(OCC)(=O)C>[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:32]=[C:33]([C:35]([F:38])([F:36])[F:37])[CH:34]=2)[CH2:10][O:11][CH2:12][C:13]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[N:5]=[N:4][N:3]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 58993687tert-Butyl 4-((3-(5-methyl-1H-tetrazol-1-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

Produkt 1

HCID 589934524-((3-(5-Methyl-1H-tetrazol-1-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

tert-Butyl 4-((3-(5-methyl-1H-tetrazol-1-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (40.0 mg, 0.08 mmol) was dissolved in a minimum amount of ethyl acetate, followed by addition of 4 N hydrochloric acid (1.5 mL). The mixture was stirred under nitrogen for 1 h. After removing the solvents, the crude mixture was precipitated in diethyl ether and filtered to afford 30.0 mg (93%) as a white powder. 1H-NMR (CDCl3, 500 MHz) δ 7.58 (s, 1H), 7.53 (s, 1H), 7.31-7.35 (m, 3H), 7.22-7.26 (m, 1H), 7.08-7.11 (m, 2H), 4.49 (s, 2H), 3.43 (s, 2H), 2.86-2.90 (m, 2H), 2.71-2.75 (m, 2H), 2.52 (s, 3H), 2.17-2.20 (m, 2H), 1.84-1.87 (m, 2H). 13C-NMR (CDCl3, 126 MHz) δ 151.5, 143.9, 143.1, 134.5, 136.6 (q, J=33.6 Hz), 128.7, 128.3, 127.2, 126.3, 127.7, 125.1 (q, J=272.6 Hz), 120.4, 80.6, 71.3, 42.6, 41.9, 33.6, 33.3. Mass spec.: 432.22 (MH)+.

Aufarbeitung

  1. customAfter removing the solvents
  2. customthe crude mixture was precipitated in diethyl ether
  3. filtrationfiltered
  4. customto afford 30.0 mg (93%) as a white powder

Quellen und Nachweise

ORD-Eintrag
ord-cfc38c33f39346819e0a17644a2531b1
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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