Methanol → Tert-Butylamine

HRID 1157984Notes

Reaction equation

HRID 1157984 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([OH:37])[CH2:24][N:25]3CC[N:28]([C:31]4[CH:36]=CC=C[CH:32]=4)CC3)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9]C.[CH3:38]O>>[C:5]([NH:25][CH2:24][CH:23]([OH:37])[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)=[CH:20][CH:19]=1)([CH3:11])([CH3:6])[CH3:4].[O:37]1[CH2:24][CH:23]1[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)=[CH:16][CH:17]=1.[C:31]([NH2:28])([CH3:36])([CH3:38])[CH3:32]

Participants

5

Reactant 2

HCID 887MethanolHCID 68643698HCID 68643698, compound

Product 3

HCID 6385Tert-ButylamineHCID 68643596HCID 68643596, compoundHCID 91507293HCID 91507293, compound

Procedure

In a similar manner to the preparation of 18, compound 34 was obtained from 4′-(2,3-epoxy-propoxy)-3,4-methylenedioxy-chalcone, 17 (1 g, 2.9 mmol) and tert-butyl amine (0.93 mL, 9 mmol) in dry methanol (80 mL). Yield 1 g (84%); mp 122-piperazine 124° C.; MS (FAB) 398 (M++1); IR (KBr) 3401, 1660; 1H NMR (300 MHz, CDCl3) δ 8.00 (d, J=8.7 Hz, 2H), 7.71 (d, J=15.6 Hz, 1H), 7.37 (d, J=15.6 Hz, 1H), 7.16 (s, 1H), 7.11 (d, J=8.1 Hz, 1H), 6.99 (d, J=8.7 Hz, 2H), 6.83 (d, J=7.8 Hz, 1H), 6.01 (s, 2H), 4.07-3.98 (m, 3H), 2.87 (dd, J=12.0 Hz, 3.9 Hz, 3.3 Hz, 1H), 2.69 (dd, J=12.0 Hz, 7.5 Hz, 7.5 Hz, 1H), 2.42 (bs, OH, NH), 1.13 (s, 9H); 13C NMR (50 MHz, CDCl3) δ 188.9, 162.9, 150.1, 148.8, 144.8, 131.9, 131.1, 129.9, 125.4, 120.3, 114.8, 109.0, 107.1, 101.9, 71.2, 68.9, 45.0, 29.4. Analyses calculated for C23H27NO5: C, 69.50; H, 6.85; N, 3.52. Found: C, 68.84; H, 6.94; N, 3.42.

Sources & evidence

ORD record
ord-db46a368fce94a21b81c86bdc25a6060
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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