Triethylamine → HCID 69309973, compound

HRID 2250127Notes

Reaction equation

HRID 2250127 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][NH:19][CH2:20]3)=[CH:15][CH:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CCN(CC)CC.[F:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([Cl:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1>>[ClH:40].[F:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([N:19]2[CH2:18][CH2:17][C:16]3[C:21](=[CH:22][C:13]([O:12][CH2:11][CH2:10][CH2:9][N:3]4[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]4)=[CH:14][CH:15]=3)[CH2:20]2)(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 69311509HCID 69311509, compound

Product 1

HCID 69309973HCID 69309973, compound

Procedure

2-(4-Fluoro-benzenesulfonyl)-7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline hydrochloride is prepared from 7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride (158 mg, 0.45 mmol), NEt3 (0.21 mL, 1.5 mmol), and 4-fluorobenzenesulfonyl chloride (115 mg, 0.55 mmol) via a procedure substantially analogous to Procedure F except that an additional SCX column purification step is performed to give 140 mg of free base product. The free base is converted to the HCl salt (150 mg, 71% yld) via a procedure substantially analogous Procedure D. MS (ES+)433.2(M+H)+ free base.

Sources & evidence

ORD record
ord-384c39e8e5ca4ea390e8d44d05339ed9
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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