Triethylamine → HCID 59438573, compound

HRID 1641028Notes

Reaction equation

HRID 1641028 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2].[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].[NH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.C(N(CC)CC)C>C(Cl)Cl.CCOCC>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13](=[O:17])[C:14]([NH:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]2)=[O:15])=[CH:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 12682914-Amino-1-Boc-piperidineHCID 4389257HCID 4389257, compound

Product 1

HCID 59438573HCID 59438573, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared according to general procedure C described in Scheme 2. N-Isopropylindole (1 g, 6 mmol) was treated with ether (10 mL), cooled to 0° C. and treated dropwise with oxalyl chloride (0.62 mL, 7 mmol). The reaction was gradually warmed to RT over a 3 h period affording a yellow precipitate. The reaction mixture was concentrated under reduced pressure and the resulting yellow solid was dissolved in DCM (20 mL) cooled to 0° C. and treated with a solution of tert-butyl 4-aminopiperidine-1-carboxylate (1.5 g, 7 mmol) and triethylamine (5.2 mL, 38 mmol) in DCM (10 mL). The reaction mixture was allowed to warm to RT and stirred for 14 h. The reaction mixture was concentrated under reduced pressure and the crude material was purified on silica gel (Biotage, 15-50% EtOAc/Hexanes, 30 min.) to provide the title compound as a yellow oil (1.3 g, 50% yield).

Workup

  1. customThe title compound was prepared
  2. temperatureThe reaction was gradually warmed to RT over a 3 h period
  3. customaffording a yellow precipitate
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe resulting yellow solid was dissolved in DCM (20 mL)
  6. temperaturecooled to 0° C.
  7. temperatureto warm to RT
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customthe crude material was purified on silica gel (Biotage, 15-50% EtOAc/Hexanes, 30 min.)

Sources & evidence

ORD record
ord-aee81f0bef8c458cb0eb8844123e0918
Source dataset
uspto-grants-2012_02
Patent number
US08114894B2

Reaction notes

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