Ammonia → Spiro(indole-3,4'-piperidin)-2(1H)-one

HRID 2262728Notes

Reaction equation

N.C([N:9]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]1=[O:23])C1C=CC=CC=1.CCO>C1COCC1>[NH:14]1[CH2:15][CH2:16][C:11]2([C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:9][C:10]2=[O:23])[CH2:12][CH2:13]1

Participants

Conditions

Temperature: -78 °C

Procedure

At −78° C., to liquid NH3 (20 ml) is added dropwise a solution of 1-benzylspiro[indole-3,4′-piperidin]-2(1H)-one (2 mmol) in THF (30 ml) and the mixture is stirred at −78° C. for 10 min. Li (42 mg, 6 mmol) is added in 3 portions and the resulting dark blue solution is stirred at −78° C. for 2 h. Anhydrous EtOH (1 ml) is added dropwise and the mixture is allowed to warm to rt overnight. Solvent is removed in vacuo and the resulting title compound (a light yellow solid) is used in the next step without further purification.

Workup

additionLi (42 mg, 6 mmol) is added in 3 portions
stirringthe resulting dark blue solution is stirred at −78° C. for 2 h
temperatureto warm to rt overnight
customSolvent is removed in vacuo
customthe resulting title compound (a light yellow solid) is used in the next step without further purification

Sources & evidence

ORD record: ord-cb7317f6541a43a3b1d383b99d8af069
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851474B2

Reaction notes

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