Hydrochloric Acid → HCID 68944597, compound

HRID 1484099Notes

Reaction equation

HRID 1484099 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][NH2:15])[CH:9]=[CH:10][CH:11]=1.[ClH:21]>C(OCC)C>[ClH:21].[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][NH2:15])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25100103HCID 25100103, compound

Product 1

HCID 68944597HCID 68944597, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of (E)-3-(3-(2,6-dimethylstyryl)phenyl)propan-1-amine (0.296 g, 1.10 mmol) in diethyl ether (15 mL) was added 1N HCl in diethyl ether (1.2 mL, 1.20 mmol), resulting in immediate precipitation of a white solid. The suspension was stirred for 1.5 h, filtered and dried under vacuum to afford 0.314 g (95%) of (E)-3-(3-(2,6-dimethylstyryl)phenyl)propan-1-amine hydrochloride as a light yellow solid: mp 135-136° C.; 1H NMR (500 MHz, CD3OD) δ 7.40 (d, J=11.0 Hz, 2H), 7.31 (t, J=7.6 Hz, 1H), 7.21 (s, 1H), 7.17-7.14 (m, 1H), 7.04 (s, 3H), 6.58 (d, J=16.6 Hz, 1H), 2.95 (t, J=7.7 Hz, 1H), 2.75 (t, J=7.6 Hz, 2H), 2.34 (s, 6H), 2.00 (quint, J=7.7 Hz, 2H), 1.90 (m, 2H); 13C NMR (75 MHz, CD3OD) δ 142.2, 139.4, 138.2, 137.1, 135.2, 130.0, 128.9, 128.7, 128.3, 127.9, 127.4, 125.4, 40.4, 33.5, 30.4, 21.2; ESI MS m/z 266 [M+H]+; HPLC (Method 2)>99% (AUC), tR=16.4 min. Calcd for C19H23N.HCl: C, 75.60; H, 8.01; N, 4.64. Found: C, 75.25; H, 7.99; N, 4.66.

Workup

  1. customresulting in immediate precipitation of a white solid
  2. filtrationfiltered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-6657c82fd5614736b046416af4eb55ff
Source dataset
uspto-grants-2016_08
Patent number
US09421210B2

Reaction notes

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