Formaldehyde → HCID 178483329, compound

HRID 2293515Notes

Reaction equation

[NH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[CH2:6][CH2:5][C:4]=2[C:3]([CH2:14][NH:15][CH3:16])=[N:2]1.[C:17]([BH3-])#N.[Na+].C=O.[OH-].[Na+]>CO.O.[Cl-].[Na+].C(OCC)(=O)C.C(O)(=O)C>[NH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[CH2:6][CH2:5][C:4]=2[C:3]([CH2:14][N:15]([CH3:17])[CH3:16])=[N:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (4,5-dihydro-1H-benzo[g]indazol-3-ylmethyl)-methylamine (3.1 g), sodium cyanoborohydride (1.1 g) and glacial acetic acid (2 cm3) in methanol (50 cm3) was cooled to 0° C. and formaldehyde solution (38% formaldehyde in methanol; 2 cm3) was added. The mixture was stirred at 0° C. for 90 minutes, with mild effervescence observed. The mixture was basified with aqueous sodium hydroxide (1 mol dm-3 ; 30 cm3), diluted with water (50 cm3) and saturated with sodium chloride before extraction with ethyl acetate (2×50 cm3). The organic phases were dried (MgSO4), filtered and concentrated to give (4,5-dihydro-1H-benzo[g]indazol-3-ylmethyl)-dimethylamine as an orange foam (3.17 g; 96%); δH (360 MHz; CDCl3) 2.35 [6H, s, N(CH3)2 ], 2.73 (2H, t, J 7.7, --CH2 --), 2.95 (2H, t, J 7.7, --CH2 --), 3.59 (2H, s, --CH2N), 7.17-7.26 (3H, m, 3 of ArH) and 7.77 (1H, d, J 7, 1 of ArH); m/z (CI+ ; NH3) 455 (M2H+ ; 3%) and 228 (MH+ ; 100).

Workup

dry with materialThe organic phases were dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-57a11504fcc64ef0aaeb801a06f30408
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686480

Reaction notes

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