Hydrochloric Acid → Benzyl Alcohol

HRID 1049065Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[CH:24][C:25]3[O:29][C:28]([C:30](=[O:32])[NH2:31])=[CH:27][C:26]=3[CH:33]=2)[CH2:18][CH2:17]1)#[N:2].[ClH:34].[CH:35]([OH:38])([CH3:37])C>C(O)C1C=CC=CC=1>[ClH:34].[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([C:22]2[CH:23]=[CH:24][C:25]3[O:29][C:28]([C:30](=[O:32])[NH2:31])=[CH:27][C:26]=3[CH:33]=2)[CH2:20][CH2:21]1)#[N:2].[CH2:35]([OH:38])[C:37]1[CH:5]=[CH:4][CH:3]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 22.5 °C

Procedure

1-[4-(5-Cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine (1 g) was dissolved in benzyl alcohol (10 ml) under inert gas atmosphere at 20-25° C. To the clear solution was added HCl in isopropanol (0.55 g, 1.2 eq). The resulting suspension was stirred for 20 h at 20-25° C. The suspension was then heated to 35° C. and maintained for 3 h. The solid was filtered, washed with acetone (2×5 mL) and dried at about 65° C. to afford 0.84 g hemi solvate of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine hydrochloride with benzyl alcohol. 1H NMR (DMSO-d6) 11.47 (br s, 1H); 10.40 (br s, 1H); 8.10 (s, 1H); 8.05, 7.63 (br s, 2H); 7.55-7.50 (m, 2H); 7.45-7.39 (m, 3H); 7.32-7.25 (m, 2.5H); 7.23-7.20 (m, 1H); 5.10 (br s, 0.5H); 4.49 (s, 1H); 3.75-3.70 (m, 2H); 3.6-3.56 (m, 2H); 3.25-3.08 (m, 6H); 2.78 (t, 2H); 1.79-1.68 (m, 4H).

Workup

temperatureThe suspension was then heated to 35° C.
temperaturemaintained for 3 h
filtrationThe solid was filtered
washwashed with acetone (2×5 mL)
customdried at about 65° C.

Sources & evidence

ORD record: ord-b53b7d30e16343cf948d07a1f37a51e6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382233B2

Reaction notes

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