Hydrochloric Acid → (S,S)-2-[4-(2,5-diaza-bicyclo[2.2.1]hept-2-ylmethyl)-phenoxy]-benzothiazole hydrochloride

HRID 384501Notes

Reaction equation

HRID 384501 reaction equation
C(OC([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)=[CH:18][CH:17]=1)=O)(C)(C)C.[ClH:32]>C(Cl)Cl>[ClH:32].[C@H:12]12[CH2:14][C@H:9]([NH:8][CH2:13]1)[CH2:10][N:11]2[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67206277(S,S)-5-[4-(Benzothiazol-2-yloxy)-benzyl]-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Product 1

HCID 67207143(S,S)-2-[4-(2,5-diaza-bicyclo[2.2.1]hept-2-ylmethyl)-phenoxy]-benzothiazole hydrochlorideYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S,S)-5-[4-(benzothiazol-2-yloxy)-benzyl]-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (8.2 g, 18.7 mmol) in CH2Cl2 (200 mL) was added HCl (4.0 N in 1,4-dioxane, 46 mL, 187 mmol). The resulting white suspension was stirred at rt for 4 h and then concentrated affording the title compound as a white solid (5.4 g, 70%). MS (ESI): mass calcd. for C19H19N3OS, 337.12; m/z found, 338.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.84 (m, 3H), 7.64 (d, J=8.3 Hz, 1H), 7.55 (m, 2H), 7.44 (m, 1H), 7.34 (m, 1H), 4.67 (br m, 3H), 4.55 (br m, 1H), 4.05 (br m, 1H), 3.84 (br d, J=13.2 Hz, 1H), 3.60 (dd, J=13.7, 2.7 Hz, 3H), 2.79 (br m, 1H), 2.34 (br d, J=12.7 Hz, 1H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-3cb827683af142808ad7a2832aada64a
Source dataset
uspto-grants-2013_02
Patent number
US08367719B2

Reaction notes

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