Triethylamine → HCID 44412733, compound

HRID 2250136Notes

Reaction equation

HRID 2250136 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CCN(CC)CC.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35](Cl)=[O:36]>C(Cl)Cl>[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[CH2:21][N:20]([C:35]([C:31]2[S:30][CH:34]=[CH:33][CH:32]=2)=[O:36])[CH2:19][CH2:18]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 69313808HCID 69313808, compound

Product 1

HCID 44412733HCID 44412733, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride salt (300 mg, 0.86 mmol) and NEt3 (0.36 mL, 2.6 mmol) in CH2Cl2 (10 mL) is added 2-thiophene carbonyl chloride (0.10 mL, 0.95 mmol). After stirring at room temperature overnight, the mixture is partitioned between EtOAc and water. The organic phase is washed with brine, dried (MgSO4), and concentrated. The residue is purified by flash chromatography [Biotage 40S SiO2, elute 20% (90/10/1 CH2Cl2/MeOH/NH4OH)/80% CH2Cl2 to 100% (90/10/1 CH2Cl2/MeOH/NH4OH)] to yield the title compound as a yellow oil (0.181 g, 55%). MS (ES+) 385.3.

Workup

  1. customthe mixture is partitioned between EtOAc and water
  2. washThe organic phase is washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography [Biotage 40S SiO2, elute 20% (90/10/1 CH2Cl2/MeOH/NH4OH)/80% CH2Cl2 to 100% (90/10/1 CH2Cl2/MeOH/NH4OH)]

Sources & evidence

ORD record
ord-c1e841e53495436e996fcc8635ae6caf
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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