Formaldehyde → HCID 18965718, compound

HRID 2226621Notes

Reaction equation

HRID 2226621 reaction equation
[ClH:1].Cl.[CH2:3]([N:5]([CH2:20][CH3:21])[CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[OH:19])[CH3:4].C=O.[C:24]([BH3-])#N.[Na+]>CO>[ClH:1].[ClH:1].[CH2:20]([N:5]([CH2:3][CH3:4])[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[OH:19])[CH3:24])[CH3:21]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18965721HCID 18965721, compound

Product 1

HCID 18965718HCID 18965718, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reductive methylation of N[3(Diethylamino)propyl]-2-hydroxy-3-methyl-5-iodo-benzylamine dihydrochloride (5 mmol, from last step) formaldehyde (5 mL, 37% solution) and sodium cyanoborohydride (0.63 g, 10 mmol) in methanol (25 mL), work-up, conversion to the dihydrochloride (conc. hydrochloric acid, 5 mL), evaporation to dryness in vacuo and crystallization of the resulting material from methanol-acetone as described for Example 1 gave the title compound as colorless crystals. Yield(overall): 1,945 g (84%); mp. 166°-168° C. NMR (CDCl3, free base): δ0.97 (t, 6H, J-6 Hz, --CH2 --CH3); 1.5-1.9 (m, 2H, --CH2 --); 2.13 (s, 3H, --CH3); 2.23 (s, 3H, --CH3); 2.3-2.7 (m, 8H, N--CH2); 3.6 (s, 2H benzylic CH2), 7.1 (d, 1H, J=1 Hz, aromatic H); 7.35 (d, 1H, J=1 Hz, aromatic H); IR (KBr): 3420, 2940, 2640, 1625, 1470, 1390, 1210 cm-1. Analysis found: C, 41.47; H, 6.24; N, 5.93. C16H29Cl2IN2O requires: C, 41.49; H, 6.31; N, 6.05.

Workup

  1. customconversion to the dihydrochloride (conc. hydrochloric acid, 5 mL), evaporation to dryness
  2. customin vacuo and crystallization of the resulting material from methanol-acetone

Sources & evidence

ORD record
ord-ae453f09be0d454d85d6bb5e45b07f20
Source dataset
uspto-grants-1994_09
Patent number
US05349063

Reaction notes

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