HCID 49760007, compound → HCID 15521808, compound

HRID 2304546Notes

Reaction equation

HRID 2304546 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:12]2[C:13]([OH:15])=O)=[CH:6][CH:5]=1>CCOCC>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH2:10][N:11]3[CH:12]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:13](=[O:15])[C:8]=2[CH:9]=1

Participants

3

Reactant 1

HCID 49760007HCID 49760007, compound

Product 1

HCID 15521808HCID 15521808, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

By the above procedure, N-(4-methoxyphenylmethyl)pipecolinic acid hydrochloride (2.98 g) was converted to 1,3,4,11a-tetrahydro-9-methoxy-2H-benzo[b]quinolizin-11(6R)-one (950 mg): mp 117-119° C. (ether); 1H NMR (300 MHz) δ 7.48 (d, J=2.7 Hz, 1 H), 7.14 (d, J=8.4 Hz, 1 H), 7.08 (dd, J=8.4, 2.7 Hz, 1 H), 3.84 (s, Me), 3.84(d, J=14.8 Hz, 1 H), 3.61 (d, J=14.8 Hz, 1 H), 3.08 (br d, J=11.1 Hz, 1 H), 2.74 (br d, J=10.1 Hz, 1 H), 2.42 (m 1 H), 2.34 (td, J=11.3, 3.6 Hz, 1 H), 1.90 (m, 1 H), 1.15-1.80 (m); 13C NMR (75 MHz) δ 195.89, 158.84, 134.60, 131.02, 127.51, 121.88, 108.96, 69.01, 56.61, 56.13, 55.52, 26.74, 25.03, 23.87; MS (EI) 231 (64, M), 203 (53), 202 (53), 174 (10), 161 (83), 148 (27), 121 (100), 120 (31); Anal. Calcd for C14H17NO2: C, 72.70; H, 7.41; N, 6.06; found C, 72.47; H, 7.47; N, 5.91.

Sources & evidence

ORD record
ord-7ae2ba63481844f681e31a9f9dbaff31
Source dataset
uspto-grants-2002_08
Patent number
US06436954B1

Reaction notes

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