Hydrochloric Acid → N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride

HRID 1518265Notes

Reaction equation

HRID 1518265 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[O:12].[ClH:30]>C(Cl)Cl.CCOCC>[ClH:30].[ClH:30].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][NH:20][CH2:19][CH2:18]2)=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59447535tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 86644320N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1A) (8.5 g, 20.75 mmol) in DCM (80 mL) was added 2N HCl in ether (80 mL). The reaction mixture was stirred at rt overnight and concentrated under reduced pressure to provide the desired product N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride (1B): LC/MS(APCI): m/z 309.9 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f8e6220373f4b1e99336743f4a193fc
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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