Sodium Carbonate → N-Boc-3-Chloropropylamine

HRID 2072821Notes

Reaction equation

HRID 2072821 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:7]([O:11][C:12](=O)[O:13]C(C)(C)C)([CH3:10])([CH3:9])[CH3:8].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[C:7]([O:11][C:12]([NH:6][CH2:5][CH2:4][CH2:3][Cl:2])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 10932310N-Boc-3-Chloropropylamine

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent2×

Conditions

Temperature
0 °C

Procedure

The compound of the title, employed as the starting material in example 1, is prepared by slowly adding a solution of 3-chloro-propylamine hydrochloride (12.98 g, 0.1 mol) in dioxane/water (100 ml 2/1 v/v) to a vigorously stirred mixture of di-(tert-butyl)carbonate (24 g, 0.11 mol), 1N Na2CO3 (100 ml) and dioxane/water (200 ml, 2/1 v/v) cooled to 0° C. When the addition is over, the reaction mixture is stirred at room temperature for an additional hour, dioxane is removed under vacuum and the aqueous phase is extracted a few times with ethyl acetate.

Workup

  1. customis prepared
  2. additionWhen the addition
  3. customdioxane is removed under vacuum
  4. extractionthe aqueous phase is extracted a few times with ethyl acetate

Sources & evidence

ORD record
ord-4d6fb86cf6ba406c881a884ea7e46f9b
Source dataset
uspto-grants-1990_04
Patent number
US04914226

Reaction notes

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