Hydrochloric Acid → HCID 68109424, compound

HRID 2179435Notes

Reaction equation

HRID 2179435 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH2:15][CH2:14][NH:13][CH2:12][C:11]=3[C:7]=2[CH:6]=[C:5]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:4]=1.[ClH:23]>ClCCl.CO>[ClH:23].[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH2:15][CH2:14][NH:13][CH2:12][C:11]=3[C:7]=2[CH:6]=[C:5]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68108546HCID 68108546, compound

Product 1

HCID 68109424HCID 68109424, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product obtained from step E (5 mg, 0.01 mmol) was converted to the hydrochloride salt by dissolving in dichloromethane and treating with 1.25 M HCl in methanol. The reaction mixture was concentrated in vacuo to give 6-methoxy-8-phenoxy-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (5.5 mg, 97%, AUC HPLC 95.9%) as a white solid: mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 8.97 (br s, 2H), 7.41-7.33 (m, 2H), 7.13-7.07 (m, 1H), 7.00-6.94 (m, 2H), 6.82 (d, J=2.4 Hz, 1H), 6.76 (d, J=2.0 Hz, 1H), 4.20 (s, 2H), 3.90 (s, 3H), 3.54-3.45 (m, 2H), 3.09-3.00 (m, 2H); APCI MS m/z 296 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-801d9a2810f94959872cd5a16be0ac4e
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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