Hydrochloric Acid → 5-Fluorospiro[indene-2,4'-piperidin]-1(3H)-one

HRID 1752234Notes

Reaction equation

HRID 1752234 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[C:6]1([CH2:11][CH2:10][N:9](C(OCC)=O)[CH2:8][CH2:7]1)[CH2:5]2.Cl>>[F:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[C:6]1([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH2:5]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 71227516Ethyl 5-fluoro-1-oxo-1,3-dihydrospiro[indene-2,4'-piperidine]-1'-carboxylate

Product 1

HCID 712121695-Fluorospiro[indene-2,4'-piperidin]-1(3H)-oneYield 113.1%

Procedure

To a stirred solution of ethyl 5-fluoro-1-oxo-1,3-dihydrospiro[indene-2,4′-piperidine]-1′-carboxylate (188 mg, 0.645 mmol) in HCl (19.61 μL, 0.645 mmol) was heated at 100° C. over night. The reaction mixture was concentrated to dryness without any further purification to give the title compound (160 mg, 97% yield). MS (ESI) [m/e, (M+H)+]=220.0 (M+H)+, HPLC retention time=0.51 minutes (Agilent 1100 HPLC system; 3.0 cm×3.0 mm×3.0 um C8 column; flow rate of 2.0 mL/min; gradient of 5-95% acetonitrile/water with 0.1% fomic acid over 2 minutes).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness without any further purification

Sources & evidence

ORD record
ord-a74ded32ba8b4a8089695e19aa91c328
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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