Acetic Acid → HCID 23458400, compound

HRID 903958Notes

Reaction equation

HRID 903958 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]([CH:14]1[O:19][CH2:18][CH2:17][NH:16][CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13].[BH4-].[Na+].[C:26]([O-])(O)=O.[Na+].[C:31](O)(=O)[CH3:32]>CC(C)=O.O>[CH:31]([N:16]1[CH2:17][CH2:18][O:19][CH:14]([CH:6]([O:5][C:4]2[CH:20]=[CH:21][CH:22]=[CH:23][C:3]=2[O:2][CH3:1])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:15]1)([CH3:32])[CH3:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 3029355HCID 3029355, compoundHCID 4311764Sodium borohydride2×

Product 1

HCID 23458400HCID 23458400, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a well stirred mixture of 2-[α-(2-methoxy-phenoxy)-2-chloro-benzyl]-morpholine (2 g) in glacial acetic acid (5.2 ml), acetone (12 ml) and water (8 ml), NaBH4 (6.024 g) was added over 1 hour maintaining the temperature near 0° C. Then more acetone (12 ml) and NaBH4 (3 g) were added; the temperature was allowed to rise to room temperature and after 30 hours the reaction mixture was poured into a solution of NaHCO3 in water, then extracted with diethyl ether. The ethereal extracts were washed with water, dried over Na2SO4 and evaporated to dryness to give 4-isopropyl-2-[α-(2-methoxy-phenoxy)-2-chloro-benzyl]-morpholine (1.85 g; yield 82.3%) .HCl m.p. 200°-240° C.

Workup

  1. additionwas added over 1 hour
  2. extractionextracted with diethyl ether
  3. washThe ethereal extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c5a604a9e03b43dda4c535fbd75b3773
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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