Hydrochloric Acid → Tamsulosin Hydrochloride

HRID 1180688

Reaction equation

HRID 1180688 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][NH:13][C@@H:14]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:27][CH3:28])=[C:21]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:22]=1)[CH3:15].[ClH:29]>C(Cl)Cl>[CH3:1][CH2:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][NH:13][C@@H:14]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:27][CH3:28])=[C:21]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:22]=1)[CH3:15].[ClH:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 129211Tamsulosin

Product 1

HCID 5362376Tamsulosin HydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tamsulosin 1 (2.011 g, 4.917 mmol) in CH2Cl2 (50 mL) was bubbled with excess dry HCl(g) at 0-5° C. for 1.0 h. The resultant precipitate was filtered and dried under vacuum at room temperature to obtain tamsulosin•HCl (2.091 g, 4.699 mmol) as white solids in 96% yield: mp (recrystallized from 50% MeOH in EtOH) 230-231° C.; specific rotation α D20=−5.3843°; 1H NMR (D2O, 400 MHz) δ 1.14-1.17 (m, 6 H, NCHCH3+OCH2CH3), 2.71-2.76 (m, 1 H, ArCHH), 2.95-3.00 (m, 1 H, ArCHH), 3.36-3.43 (m, 2 H, NCH2), 3.53-3.55 (m, 1 H, NCH), 3.75 (s, 3 H, OCH3), 3.94-3.97 (m, 2 H, MeCH2O), 4.04-4.19 (m, 2 H, OCH2CH2), 6.84-6.96 (m, 5 H, ArH), 7.35 (d, J=8.8 Hz, 1 H, ArH), 7,54 (s, 1 H, ArH); IR (neat) 3304 (m), 3168 (m), 2981 (m), 1610 (m), 1589 (m), 1500 (s), 1458 (m), 1392 (m), 1339 (s), 1251 (s), 1215 (s), 1160 (s), 1128 (s), 1072 (m), 1046 (m), 1018 (m), 820 (m), 749 (s), 718 (m) cm−1.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-5684f83d057a425d9f441ba2dc6f629d
Source dataset
uspto-grants-2007_10
Patent number
US07282606B2

Linked notes

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