Formaldehyde → HCID 59752627, compound

HRID 2106315Notes

Reaction equation

HRID 2106315 reaction equation
[C:1]1([N:7]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:15]3[C:9]([CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:27](C)=O.[Na+]>C(Cl)Cl.[OH-].[Na+]>[CH3:27][N:12]1[CH2:11][CH2:10][C:9]2[C:15](=[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 24873257HCID 24873257, compound

Product 1

HCID 59752627HCID 59752627, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 33.5 mg of 2,3-diphenyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene (Example 176, Step D) in 5 mL of CH2Cl2 were added 0.15 g of paraformaldehyde and 0.15 g of NaBH(OAc)3. The mixture was stirred at RT for 12 h and was diluted with 20 mL of 1 M NaOH. After stirring for 3 h, the mixture was extracted with CH2Cl2 (2×10 mL) and the combined organic layers were concentrated. Chromatography on SiO2 (0 to 5% 2 M NH3 in MeOH/CH2Cl2) gave 22.3 mg of the title compound as a white solid. MS (ESI): exact mass calculated for C20H21N3, 303.17; found, m/z 304.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.35-7.30 (m, 3H), 7.27-7.21 (m, 2H), 7.20-7.16 (m, 3H), 7.15-7.12 (m, 2H), 3.06-3.02 (m, 2H), 2.83-2.79 (m, 2H), 2.72-2.67 (m, 4H), 2.50 (s, 3H).

Workup

  1. stirringAfter stirring for 3 h
  2. extractionthe mixture was extracted with CH2Cl2 (2×10 mL)
  3. concentrationthe combined organic layers were concentrated

Sources & evidence

ORD record
ord-e3832bdd65044a119e01ea464e866e2d
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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