Diethyl Ether → HCID 59536270, compound

HRID 445296Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][CH2:6][NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[K+].C(OCC)C>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:20](=[CH:21][CH:22]=1)[C:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[N:7][CH2:6][CH2:5]2

Participants

Conditions

Temperature: 170 °C

Procedure

A suspension of N-(3-fluorophenethyl)-4-(trifluoromethyl)benzamide (2.8 g, 8.9 mmol) and phosphoric pentoxide (0.6 g, 0.45 mmol) in polyphosphoric acid (62.0 g, 8.9 mmol) was heated at 170° C. for 75 min. The hot reaction mixture was poured into ice and KOH (20% W/V, 50 mL) was added followed by diethyl ether (100 mL) and stirred for 5 mins. Additional KOH was added until pH˜11.0 was achieved. Then, EtOAc (200 mL) was added and the mixture continued stirring at RT for an additional 5 min. and the ethyl acetate layer was separated. The aqueous layer was back-extracted with ethyl acetate (3×200 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, and concentrated under vacuum to provide 6-fluoro-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline as a yellow oil. MS (ESI pos. ion) m/z: 294 (M+H).

Workup

additionwas added
stirringthe mixture continued stirring at RT for an additional 5 min.
customthe ethyl acetate layer was separated
extractionThe aqueous layer was back-extracted with ethyl acetate (3×200 mL)
dry with materialThe combined ethyl acetate layers were dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-1e64de70553146eaba4f725e463e3eb9
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476297B2

Reaction notes

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