Hydrochloric Acid → HCID 86614343, compound

HRID 2236105Notes

Reaction equation

HRID 2236105 reaction equation
Cl.[CH2:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH2:5][CH2:4][NH:3]1.CCN([CH:27]([CH3:29])[CH3:28])C(C)C.Cl>ClCCl>[CH2:19]([O:18][C:16]([N:3]1[CH2:4][CH2:5][C:6]2[N:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[CH2:2]1)=[O:17])[C:28]1[CH:27]=[CH:29][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 71552668Ethyl (1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate hydrochloride

Product 1

HCID 86614343HCID 86614343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 1 (29.5 mg, 0.10 mmol) and DIEA (51 μl, 0.30 mmol) in dichloromethane (1 ml) is added benzyl chlorofornate (16 μl, 0.11 mmol). The reaction mixture is stirred at rt for 1 h, 1 N aqueous HCl (2 ml). The aqueous layer is extracted twice with dichloromethane. The combined organic layers are washed with water, saturated NaHCO3 solution, then are concentrated to dryness to afford crude ethyl (2-benzyloxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate: tR (LC-1) 2.52 min; ESI-MS (positive ion): m/z 393.19 [M]+ (calcd 392.45 for C23H24N2O4).

Workup

  1. extractionThe aqueous layer is extracted twice with dichloromethane
  2. washThe combined organic layers are washed with water, saturated NaHCO3 solution
  3. concentrationare concentrated to dryness

Sources & evidence

ORD record
ord-6be3c81203404928b1b971161f5037c8
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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