HCID 10134015, compound → HCID 69308514, compound

HRID 2250131Notes

Reaction equation

HRID 2250131 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.[ClH:28].O1CCOCC1>C(Cl)Cl>[ClH:28].[ClH:28].[N:22]1([CH2:21][CH2:20][CH2:19][O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][NH:8][CH2:17][CH2:16]3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 10134015HCID 10134015, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 69308514HCID 69308514, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round-bottom flask, equipped with stir bar and septum, is placed 6-(3-piperidin-1-yl-propoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (1 g, 2.6 mmol), DCM (20 mL) and 4M HCl/dioxane (5 mL). The reaction is allowed to stir at room temperature for 3 h. After this time, the reaction is concentrated, dissolved in MeOH and concentrated again affording 6-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride as a white solid (800 mg, 87%). Mass spec hit M+1, 275; LCMS>95% @ 230 nm and ELSD.

Workup

  1. customTo a round-bottom flask, equipped
  2. stirringto stir at room temperature for 3 h
  3. concentrationAfter this time, the reaction is concentrated
  4. dissolutiondissolved in MeOH
  5. concentrationconcentrated again affording 6-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride as a white solid (800 mg, 87%)

Sources & evidence

ORD record
ord-7369bbb1e32e468c98f37d608c399968
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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