Triethylamine → HCID 44412667, compound

HRID 2250121Notes

Reaction equation

HRID 2250121 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.[CH:30]([N:33]=[C:34]=[O:35])([CH3:32])[CH3:31]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:30]([NH:33][C:34]([N:19]1[CH2:18][CH2:17][C:16]2[C:21](=[CH:22][C:13]([O:12][CH2:11][CH2:10][CH2:9][N:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)=[CH:14][CH:15]=2)[CH2:20]1)=[O:35])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 69311509HCID 69311509, compound

Product 1

HCID 44412667HCID 44412667, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A 10 mL CH2Cl2 solution of 7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride (254 mg, 0.73 mmol), NEt3 (0.20 mL, 1.4 mmol), isopropyl isocyanate (192 mg, 2.2 mmol), and 4-dimethylaminopyridine (12 mg, 0.1 mmol) is stirred under N2, at room temperature for 18 hours. The reaction mixture is concentrated and the residue is purified by chromatography (SCX-MeOH wash, elute 2M NH3/MeOH; then SiO2; 0-10% MeOH/CH2Cl2/1% NH4OH gradient) to give pure product (110 mg, 42% yld). MS(ES+) 360.2(M+H)+.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified by chromatography (SCX-MeOH
  3. washwash
  4. washelute 2M NH3/MeOH
  5. custom0-10% MeOH/CH2Cl2/1% NH4OH gradient) to give pure product (110 mg, 42% yld)

Sources & evidence

ORD record
ord-1c28fe3c886e43d79d04623e41ed3fc7
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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