1,4-Dimethy-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine → 1-(10-Acetyl-6,7,8,9,9a,10-hexahydro-5aH-pyrido[3,4-b]quinoxalin-5-yl)ethanone

HRID 1670654Notes

Reaction equation

HRID 1670654 reaction equation
CN1CCN(C)[C:4]2[CH:9]=NC=[CH:12][C:3]1=2.[C:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:24])[CH3:23])[C:18]2[CH:25]=[CH:26][N:27]=[CH:28][C:17]1=2)(=[O:15])[CH3:14]>CO>[C:13]([N:16]1[CH:21]2[CH:20]([CH2:12][CH2:3][CH2:4][CH2:9]2)[N:19]([C:22](=[O:24])[CH3:23])[C:18]2[CH:25]=[CH:26][N:27]=[CH:28][C:17]1=2)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 441857941,4-Dimethy-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine2×HCID 597630781-(4-Acetyl-3,4-dihydro-2H-pyrido[3,4-b]pyrazin-1-yl)ethanone

Product 1

HCID 673385621-(10-Acetyl-6,7,8,9,9a,10-hexahydro-5aH-pyrido[3,4-b]quinoxalin-5-yl)ethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

27 (1.20 g, 6.34 mmol), 40 ml of pyridine, 30 ml (32.36 g, 317 mmol, ρ=1.082 g/ml) of acetic anhydride and 0.234 g (25 mol %) of PPY were introduced into a 250 ml round-bottomed flask while cooling in ice. The reaction mixture was heated to an oil bath temperature of 100° C. and maintained at this temperature for 48 hours. The reaction was followed by TLC on basic aluminum oxide (EtOAC/MeOH, 10:1). After cooling to room temperature, the solvent was distilled off under reduced pressure and the crude product obtained was purified by flash chromatography on basic aluminum oxide (EtOAc/MeOH, 10:1). This gave a dark yellow solid (1.17 g, 4.31 mmol, 68%). Rf=0.45 (EtOAC/MeOH, 10:1). 1H NMR: (400 MHz, CDCl3): δ=1.34 (m, 4H), 1.60 (d, 4H), 2.23 (s, 3H, H3C—CO—N), 2.27 (s, 3H, H3C—CO—N), 4.74 (m, 1H), 4.85 (m, 1H), 7.25 (d, 3J=5.6 Hz, 1H, H-4), 8.41 (d, 3J=5.6 Hz, H-3), 8.49 (s, 1H, H-1) ppm. 13C NMR (75 Hz, CDCl3): δ=21.7, 21.9 (C-7,8), 23.1, 23.6 (H3C—CO—N), 28.4, 28.5 (C-6,9), 55.2, 56.0 (CH, C-5a,9a), 119.6 (C-4), 130.8 (Cq, C-10a), 141.6 (Cq, C-4a), 147.1, 147.2 (C-1, C-3) 169.1, 169.2 (C═O) ppm. GC-MS (EI): RT 10.45 min, m/e (%) 274 (13), 273 (M+, 58), 232 (15), 231 (100), 230 (42), 216 (5), 214 (5), 213 (5), 203 (3), 202 (4), 190 (13), 189 (84), 188 (45), 173 (5), 172 (6), 160 (7), 159 (5), 158 (5), 147 (8), 146 (40) 134 (6), 133 (13), 132 (15), 120 (7), 43 (9); IR (neat): ν=2940 (m), 1660 (vs), 1587 (m), 1559 (w), 1498 (s), 1448 (w), 1427 (w), 1388 (m), 1353 (w), 1337 (m), 1289 (s); 1270 (s), 1248 (s), 1248 (m), 1220 (w), 1183 (w), 1102 (w), 1036 (m), 978 (m), 857 (w), 839 (w) 777 (w) cm−1. HRMS (EI): calculated for C11H15N3 273.1477 [M+], found: 273.1482.

Sources & evidence

ORD record
ord-a9461a3eb0fd480895797fe80bcfc0f0
Source dataset
uspto-grants-2011_08
Patent number
US07994169B2

Reaction notes

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