Sodium borohydride → N-2-Hydroxyethyl-N-2-hydroxyoctadecyl-N-methyl amine

HRID 1708344Notes

Reaction equation

HRID 1708344 reaction equation
[OH:1][C:2]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:7][CH2:6][CH2:5][N:4]([CH3:8])[CH2:3]1.[BH4-].[Na+]>CO>[OH:7][CH2:6][CH2:5][N:4]([CH2:3][CH:2]([OH:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 103373962-Hydroxy-4-methyl-2-hexadecylmorpholine

Product 1

HCID 19694636N-2-Hydroxyethyl-N-2-hydroxyoctadecyl-N-methyl amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To suspension of 2-Hydroxy-4-methyl-2-hexadecylmorpholine (5 g, 14.66 mmol) in methanol (150 mL) at 0° C. was added NaBH4 (1.1 g, 29 mmol over a period of 10 min. The reaction mixture was brought to room temperature slowly and stirred at room temperature for 12 hours. Additional NnBH4 (200 mg, 5.2 mmol) was added at room temperature and stirred for 2 hours at room temperature. Methanol was removed by rotavop and the residue was treated with water (100 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic phase was washed with water, brine and dried over Na2SO4. Evaporation of the solvent gave a product which was used without further purification in the next step. Yield 4.92g, 98%. NMR 1H (CDCl3, 200 MHz) 0.88 (3H, t, CH3), 1.26 (28H, s, CH2), 1.40 (2H, m, CH2), 2.32 (3H, s, N--CH3), 2.3-2.7 (4H, m, CH2), 3.66 (3H, m, CH2OH, CHOH). NMR 13C (CDCl3, 50 MHz) 67.6, 64.2, 59.7, 59.3, 42.5, 34.9, 31.9, 29.6, 29.3, 25.6, 22.6, 14.0. IR (KBr) cm-1 3436, 2918, 2850, 1469, 1087, 880, 722.

Workup

  1. customwas brought to room temperature
  2. additionAdditional NnBH4 (200 mg, 5.2 mmol) was added at room temperature
  3. stirringstirred for 2 hours at room temperature
  4. customMethanol was removed by rotavop
  5. additionthe residue was treated with water (100 mL)
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. washThe combined organic phase was washed with water, brine
  8. dry with materialdried over Na2SO4
  9. customEvaporation of the solvent
  10. customgave a product which
  11. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-e13c9afcbc2a4dc9ba496ae083a4503d
Source dataset
uspto-grants-1994_10
Patent number
US05358942

Reaction notes

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