Triethylamine → HCID 59640602, compound

HRID 2250125Notes

Reaction equation

HRID 2250125 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.[C:30]([C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1)#[N:31]>>[C:30]([C:32]1[CH:33]=[CH:34][C:35]([S:38]([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:40])=[O:39])=[CH:36][CH:37]=1)#[N:31]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 69311509HCID 69311509, compound

Product 1

HCID 59640602HCID 59640602, compound

Procedure

2-(4-Cyanobenzenesulfonyl)-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 (175 mg, 0.5 mmol), NEt3 (0.25 mL, 1.8 mmol), and 4-cyanobenzenesulfonyl chloride (121 mg, 0.60 mmol) via a procedure substantially analogous to Procedure F except that an additional SCX column purification step is performed to give the product (157 mg, 71% yld). MS(ES+) 440.1(M+H)+.

Workup

  1. customto give the product (157 mg, 71% yld)

Sources & evidence

ORD record
ord-18750a30edfa4980be6f1f8e4f10dd2c
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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