Formaldehyde → HCID 59657570, compound

HRID 2055544Notes

Reaction equation

HRID 2055544 reaction equation
Cl.[CH2:2]1[C:7]2=[C:8]([C:15]([N:17]3[CH2:22][CH2:21][C:20]4([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[CH2:24][O:23]4)[CH2:19][CH2:18]3)=[O:16])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][NH:3]1.[CH2:31](N(CC)CC)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:31][N:3]1[CH2:4][CH2:5][N:6]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8]([C:15]([N:17]3[CH2:22][CH2:21][C:20]4([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[CH2:24][O:23]4)[CH2:19][CH2:18]3)=[O:16])=[C:7]2[CH2:2]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 69014875HCID 69014875, compound

Product 1

HCID 59657570HCID 59657570, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.050 g (0.12 mmol) 1′-(1,2,3,4-tetrahydropyrazino[1,2-a]indol-10-ylcarbonyl)-3H-spiro[2-benzofuran-1,4′-piperidine]hydrochloride, 0.033 ml (0.24 mmol) triethylamine and 0.028 g (0.94 mmol) paraformaldehyde in 2 ml methanol was heated at reflux for 1 h. The reaction mixture was cooled to 0° C. on an ice-water bath and treated with 0.011 g (0.18 mmol) sodium cyanoborohydride. After completed addition the mixture was allowed to warm to room temperature and stirred for 2 h. Quenching with water and dilution with 2 M aqueous sodium carbonate solution was followed by extraction with dichloromethane (2×50 ml). The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.036 g, 76%) as an off-white solid.

Workup

  1. temperatureat reflux for 1 h
  2. additionaddition the mixture
  3. temperatureto warm to room temperature
  4. customQuenching with water and dilution with 2 M aqueous sodium carbonate solution
  5. extractionwas followed by extraction with dichloromethane (2×50 ml)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-1b94387c9c264b449f1351f62b6ad2f8
Source dataset
uspto-grants-2008_02
Patent number
US07332501B2

Reaction notes

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