Formic Acid → HCID 12595611, compound

HRID 245584Notes

Reaction equation

HRID 245584 reaction equation
Cl.[CH3:2][NH:3][C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1.[OH-].[Na+].[CH:22](O)=O.C=O>O.CC1CCCO1>[CH3:2][N:3]([CH3:22])[C:4]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:5][CH2:6][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 12595583N-methyl-8-phenyl-1,4-dioxaspiro[4.5]decan-8-amine hydrochloride

Product 1

HCID 12595611HCID 12595611, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

N-methyl-8-phenyl-1,4-dioxaspiro[4.5]decan-8-amine hydrochloride (15 g, 59 mmol) was taken up in water (37 ml) and 2-methyltetrahydrofuran (57 ml). The free base was released by adding NaOH aq (32%, to pH>12). The organic phase was concentrated at 45° C. at reduced pressure (<10 mbar). The residue was taken up in isopropanol (8 ml) and added dropwise to formic acid (7 ml, 0.19 mol) at up to 65° C. At 65° C., formaldehyde solution (5.8 g, 0.1 mol) was added swiftly and the batch was stirred overnight (approximately 16 h) at 65° C. The batch was concentrated at 80° C. and approximately 20 mbar. The remaining raw product was used in the next step without purification.

Workup

  1. concentrationThe organic phase was concentrated at 45° C. at reduced pressure (<10 mbar)
  2. concentrationThe batch was concentrated at 80° C.
  3. customThe remaining raw product was used in the next step without purification

Sources & evidence

ORD record
ord-54fc1be5054a42aa90c3959d45c94bf4
Source dataset
uspto-grants-2014_02
Patent number
US08658827B2

Reaction notes

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