Triethylamine → HCID 59640497, compound

HRID 2250129Notes

Reaction equation

HRID 2250129 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:32]=[C:33]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=[CH:35][CH:36]=1>>[F:30][C:31]1[CH:32]=[C:33]([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:34]=[CH:35][CH:36]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 69311509HCID 69311509, compound

Product 1

HCID 59640497HCID 59640497, compound

Procedure

2-(3-Fluoro-benzenesulfonyl)-7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline is prepared from 7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride (104 mg, 0.3 mmol), NEt3 (0.14 mL, 1.1 mmol), and 3-fluorobenzenesulfonyl chloride (80 mg, 0.41 mmol) via a procedure substantially analogous to Procedure F except that an additional SCX column purification step is performed to give the free base product (90 mg, 70% yld) as an off-white solid. MS (ES+) 433.2(M+H)+.

Workup

  1. customto give the free base product (90 mg, 70% yld) as an off-white solid

Sources & evidence

ORD record
ord-7bccedeeea814f8390f6294314b462fe
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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