Hydrochloric Acid → 2-[6-(Trifluoromethyl)pyridin-3-yl]propan-2-amine--hydrogen chloride (1/1)

HRID 1672524Notes

Reaction equation

[CH3:1][C:2]([NH2:14])([C:4]1[CH:5]=[N:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1)[CH3:3].[ClH:15]>CC(C)=O>[ClH:15].[CH3:3][C:2]([NH2:14])([C:4]1[CH:5]=[N:6][C:7]([C:10]([F:12])([F:13])[F:11])=[CH:8][CH:9]=1)[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 1-methyl-1-(6-trifluoromethyl-pyridin-3-yl)-ethylamine from Preparation F (1.0 g, 4.9 mmol) in acetone (10 mL) at ambient temperature and stir for 5 minutes. Add concentrated (12.18 N) hydrochloric acid (0.4 mL, 4.9 mmol) drop-wise with continued stirring, and observe the formation of a white solid. Cool the reaction mixture to 0° C. and continue stirring for 30 minutes. Filter the resultant solid and rinse with cold acetone (2 mL). Dry under vacuum at 40° C. to provide the titled compound (0.73 g, 62%) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 9.17 (s (br), 3H), 9.02 (d, 1H, J=2.4 Hz), 8.32 (dd, 1H, J=8.0, 2.0 Hz), 7.97 (d, 1H, J=8.4 Hz), 1.71 (s, 6H); 13C NMR (100 MHz, DMSO-d6) δ 148.0, 146.2 (q, JCF=34.0 Hz), 142.4 (d, JCF=0.8 Hz), 136.0, 121.9 (q, JCF=273 Hz), 120.8 (t, JCF=2.6 Hz), 54.9, 27.5.

Workup

additionAdd
stirringcontinue stirring for 30 minutes
filtrationFilter the resultant solid
washrinse with cold acetone (2 mL)
customDry under vacuum at 40° C.

Sources & evidence

ORD record: ord-f84c36f05bbb4330a712c163686c3fc8
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998985B2

Reaction notes

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